JPH0959292A - Process for producing 4-aminopyrimidine nucleoside - Google Patents
Process for producing 4-aminopyrimidine nucleosideInfo
- Publication number
- JPH0959292A JPH0959292A JP24092795A JP24092795A JPH0959292A JP H0959292 A JPH0959292 A JP H0959292A JP 24092795 A JP24092795 A JP 24092795A JP 24092795 A JP24092795 A JP 24092795A JP H0959292 A JPH0959292 A JP H0959292A
- Authority
- JP
- Japan
- Prior art keywords
- nucleoside
- aminopyrimidine
- formula
- producing
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Landscapes
- Saccharide Compounds (AREA)
Abstract
(57)【要約】
【課題】 ４−アミノピリミジンヌクレオシドの簡
便な製造法の提供を目的とする。
【解決手段】 式［Ｉ］で表される４−アミノピリミジ
ンヌクレオシドの製造法であって、式［ＩＩ］で表され
る４−ヒドロキシピリミジンヌクレオシドの糖部水酸基
をトリメチルシリル基で保護した後、オキシ塩化リンま
たは４−クロロフェニルホスホロジクロリデートと反応
させ、得られた中間体を単離することなくアンモニア水
と反応させてトリメチルシリル基の除去と塩基部４位の
アミノ化を行い式［Ｉ］で表される４−アミノピリミジ
ンヌクレオシドを得ることを特徴とする４−アミノピリ
ミジンヌクレオシドの製造法に関する。
【化１】
【化２】
（式中、Ｒ1は水素原子、低級アルキル基、ハロゲン原
子を示し、Ｒ2、Ｒ3、Ｒ4およびＲ5は、同一であっても
異なっていてもよく、水素原子または水酸基を示す。）(57) Abstract: An object of the present invention is to provide a simple method for producing 4-aminopyrimidine nucleoside. A method for producing a 4-aminopyrimidine nucleoside represented by the formula [I], which comprises protecting the hydroxyl group of the sugar moiety of the 4-hydroxypyrimidine nucleoside represented by the formula [II] with a trimethylsilyl group, Reaction with phosphorus chloride or 4-chlorophenyl phosphorodichloridate and reaction of the resulting intermediate with aqueous ammonia without isolation to remove the trimethylsilyl group and amination of the 4-position of the base moiety The present invention relates to a method for producing 4-aminopyrimidine nucleoside, which comprises obtaining the represented 4-aminopyrimidine nucleoside. Embedded image Embedded image (In the formula, R 1 represents a hydrogen atom, a lower alkyl group or a halogen atom, and R 2 , R 3 , R 4 and R 5 may be the same or different and represent a hydrogen atom or a hydroxyl group. )
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、４−アミノピリミ
ジンヌクレオシドのワンポットによる簡便な製造法に関
するものである。TECHNICAL FIELD The present invention relates to a simple one-pot method for producing 4-aminopyrimidine nucleosides.
【０００２】[0002]
【従来の技術】従来、４−アミノピリミジンヌクレオシ
ドの代表的な製造法としては、４−ヒドロキシピリミジ
ンヌクレオシドの糖部水酸基を適当な保護基で保護した
後、塩基部４位に１，２，４-トリアゾール基または３
−ニトロ−１，２，４-トリアゾール基に導入した後、
アンモニア水で処理する方法（J.Chem.Soc.,PerkinTran
sI,1982,p.1171-1176、J.Org.Chem.,1982,47,p.3623-36
28）、シリル基で水酸基を保護した後、塩基部４位にベ
ンジルアミノ基を導入し、最後にベンジル基を脱離する
方法（日本薬学会第１１３年会講演要旨集、１９９３、
ｐ．１３２）などが報告されている。2. Description of the Related Art Conventionally, as a typical method for producing 4-aminopyrimidine nucleosides, 4-hydroxypyrimidine nucleoside is protected at its sugar moiety hydroxyl group with an appropriate protecting group, and then 1,2,4 at the 4-position of the base moiety. -Triazole group or 3
After introduction into the -nitro-1,2,4-triazole group,
Method of treating with ammonia water (J. Chem. Soc., PerkinTran
sI, 1982, p.1171-1176, J.Org.Chem., 1982,47, p.3623-36
28), after protecting the hydroxyl group with a silyl group, introducing a benzylamino group at the 4-position of the base moiety and finally eliminating the benzyl group (Abstracts of the 113th Annual Meeting of the Pharmaceutical Society of Japan, 1993,
p. 132) and the like have been reported.
【０００３】[0003]
【発明が解決しようとする課題】しかしながら、上記従
来法はいずれも多くの工程を経て初めて目的とする４−
アミノピリミジンヌクレオシドを取得するという方法で
あり、必ずしも簡便な方法とは言えなかった。したがっ
て、本発明は、４−アミノピリミジンヌクレオシドの簡
便な製造法の提供を目的とするものである。However, all of the above-mentioned conventional methods are aimed at only after many steps have been carried out.
It was a method of obtaining aminopyrimidine nucleoside, and was not necessarily a simple method. Therefore, an object of the present invention is to provide a simple method for producing 4-aminopyrimidine nucleoside.
【０００４】[0004]
【課題を解決するための手段】本発明者らは、上述の目
的を達成するために鋭意研究を重ねた結果、４−ヒドロ
キシピリミジンヌクレオシドから簡便な方法で４−アミ
ノピリミジンヌクレオシドを合成できることを見いだ
し、本発明を完成させた。すなわち、本発明は、式
［Ｉ］Means for Solving the Problems As a result of intensive studies to achieve the above object, the present inventors have found that 4-aminopyrimidine nucleoside can be synthesized from 4-hydroxypyrimidine nucleoside by a simple method. The present invention has been completed. That is, the present invention provides the formula [I]
【０００５】[0005]
【化３】 Embedded image
【０００６】（式中、Ｒ1は水素原子、低級アルキル
基、ハロゲン原子を示し、Ｒ2、Ｒ3、Ｒ4およびＲ5は、
同一であっても異なっていてもよく、水素原子または水
酸基を示す。）で表される４−アミノピリミジンヌクレ
オシドの製造法であって、式［ＩＩ］(In the formula, R 1 represents a hydrogen atom, a lower alkyl group or a halogen atom, and R 2 , R 3 , R 4 and R 5 are
They may be the same or different and represent a hydrogen atom or a hydroxyl group. ), A method for producing a 4-aminopyrimidine nucleoside represented by the formula [II]
【０００７】[0007]
【化４】 Embedded image
【０００８】（式中、Ｒ1、Ｒ2、Ｒ3、Ｒ4およびＲ5は
前記と同意義。）で表される４−ヒドロキシピリミジン
ヌクレオシドの糖部水酸基をトリメチルシリル基で保護
した後、オキシ塩化リンまたは４−クロロフェニルホス
ホロジクロリデートと反応させ、得られた中間体を単離
することなくアンモニア水と反応させてトリメチルシリ
ル基の除去と塩基部４位のアミノ化を行い上記式［Ｉ］
で表される４−アミノピリミジンヌクレオシドを得るこ
とを特徴とする４−アミノピリミジンヌクレオシドの製
造法に関するものである。(Wherein R 1 , R 2 , R 3 , R 4 and R 5 have the same meanings as defined above), the hydroxyl group of the 4-hydroxypyrimidine nucleoside sugar moiety is protected with a trimethylsilyl group, and then The reaction with phosphorus chloride or 4-chlorophenyl phosphorodichloridate, the resulting intermediate is reacted with aqueous ammonia without isolation to remove the trimethylsilyl group and to aminate the 4-position of the base moiety to give the above formula [I].
The present invention relates to a method for producing 4-aminopyrimidine nucleoside, which comprises obtaining 4-aminopyrimidine nucleoside.
【０００９】[0009]
【発明の実施の形態】本発明方法における原料化合物は
式［ＩＩ］で表される４−ヒドロキシピリミジンヌクレ
オシドである。式中、Ｒ1で表される低級アルキル基と
しては、メチル、エチル、プロピル、イソプロピルなど
の炭素数１〜５程度のアルキル基を、ハロゲン原子とし
てはフッ素、ヨウ素、臭素または塩素をそれぞれ例示す
ることができる。このような原料化合物は公知化合物で
あり、市販品か、常法にしたがって調製したものを本発
明方法に使用すればよい。BEST MODE FOR CARRYING OUT THE INVENTION The starting compound in the method of the present invention is a 4-hydroxypyrimidine nucleoside represented by the formula [II]. In the formula, examples of the lower alkyl group represented by R 1 include an alkyl group having about 1 to 5 carbon atoms such as methyl, ethyl, propyl and isopropyl, and examples of the halogen atom include fluorine, iodine, bromine and chlorine. be able to. Such raw material compounds are known compounds, and commercially available products or those prepared by a conventional method may be used in the method of the present invention.
【００１０】本発明方法は、まず原料化合物の水酸基を
トリメチルシリル基で保護した後、続けてオキシ塩化リ
ンまたは４−クロロフェニルホスホロジクロリデートと
反応させる。トリメチルシリル基の導入は常法に従って
行えばよい。たとえば、ピリジンまたはジメチルアミノ
ピリジンの単独溶媒中、もしくはピリジンまたはジメチ
ルアミノピリジンとジメチルホルムアミド、アセトニト
リル、塩化メチレンなどとの混合溶媒中、原料化合物１
モルに対してトリメチルシリルクロリドを１〜１０モル
用い、室温で０．５〜２時間程度攪拌反応させることに
より実施できる。In the method of the present invention, first, the hydroxyl group of the raw material compound is protected with a trimethylsilyl group, and subsequently, it is reacted with phosphorus oxychloride or 4-chlorophenyl phosphorodichloridate. The trimethylsilyl group may be introduced according to a conventional method. For example, starting compound 1 in a single solvent of pyridine or dimethylaminopyridine or in a mixed solvent of pyridine or dimethylaminopyridine with dimethylformamide, acetonitrile, methylene chloride, etc.
It can be carried out by using 1 to 10 mol of trimethylsilyl chloride per mol and stirring at room temperature for 0.5 to 2 hours.
【００１１】トリメチルシリル化した原料化合物とオキ
シ塩化リンまたは４−クロロフェニルホスホロジクロリ
デートとの反応は、原料化合物１モルに対して１〜５モ
ルのオキシ塩化リンまたは４−クロロフェニルホスホロ
ジクロリデートを使用し、０〜５０℃で１〜１０時間程
度攪拌反応させることにより実施することができる。For the reaction between the trimethylsilylated starting compound and phosphorus oxychloride or 4-chlorophenylphosphorodichloridate, 1 to 5 mol of phosphorus oxychloride or 4-chlorophenylphosphorodichloridate is used per 1 mol of the starting compound. However, it can be carried out by stirring and reacting at 0 to 50 ° C. for about 1 to 10 hours.
【００１２】このようにして得られた中間体単離するこ
となく、引き続きアンモニア水と反応させ、トリメチル
シリル基を除去後またはトリメチルシリル基の除去と同
時に塩基部４位をアミノ化する。すなわち、反応液に原
料化合物１モルに対して１０〜１００モル相当のアンモ
ニア水を添加し、０℃〜７０℃で１〜１０時間程度攪拌
することにより実施できる。The thus obtained intermediate is not isolated but is subsequently reacted with aqueous ammonia to aminate the 4-position of the base moiety after removing the trimethylsilyl group or simultaneously with removing the trimethylsilyl group. That is, it can be carried out by adding 10 to 100 mol of ammonia water to 1 mol of the raw material compound to the reaction liquid and stirring at 0 ° C. to 70 ° C. for about 1 to 10 hours.
【００１３】このようにして得られた目的化合物［Ｉ］
は、ヌクレオシドの通常の単離精製法（たとえば、イオ
ン交換カラムクロマトグラフィー、吸着カラムクロマト
グラフィーなどの各種クロマトグラフィー法、再結晶法
など）を適宜組み合せて単離精製することができる。The target compound [I] thus obtained
Can be isolated and purified by an appropriate combination of ordinary isolation and purification methods for nucleosides (for example, various chromatography methods such as ion exchange column chromatography, adsorption column chromatography, recrystallization method and the like).
【００１４】[0014]
【発明の効果】本発明方法は、従来の方法と比べて操作
が簡便で、反応条件も穏和で、しかもワンポットで目的
とする４−アミノピリミジンヌクレオシドを製造するこ
とができ、４−アミノピリミジンヌクレオシドの製造方
法として極めて実用的な優れた方法である。INDUSTRIAL APPLICABILITY The method of the present invention is simpler in operation than conventional methods, the reaction conditions are mild, and the desired 4-aminopyrimidine nucleoside can be produced in one pot. It is an extremely practical and excellent method for producing
【００１５】[0015]
【実施例】以下、本発明を実施例をあげて具体的に説明
するが、本発明はこれらによって何等限定されるもので
はない。 実施例１：シチジン（式［Ｉ］、Ｒ1＝Ｒ2＝Ｒ4＝Ｈ、
Ｒ3＝Ｒ5＝ＯＨ）の合成ウリジン２.４４ｇのピリジン
５０ｍｌ溶液にＴＭＳクロリド５.１ｍｌを加え室温で
１時間攪拌した後、オキシ塩化リン２ｍｌを加え、更に
４時間室温で攪拌した。この反応液に冷水５ｍｌを０℃
で加え３０分攪拌した後、２０ｍｌの２５％アンモニア
水を加え、５０℃で２時間攪拌した。この反応液を減圧
濃縮した後、イオン交換樹脂（ＰＫ２１６）で精製し、
水-エタノールから結晶化させて目的化合物２.０４ｇ
（８３.９％）を得た。EXAMPLES Hereinafter, the present invention will be described specifically with reference to examples, but the present invention is not limited thereto. Example 1: Cytidine (formula [I], R 1 = R 2 = R 4 = H,
R 3 = R 5 = OH) After stirring for 1 hour at room temperature was added the TMS chloride 5.1ml of pyridine 50ml solution synthesis uridine 2.44g of added phosphorus oxychloride 2 ml, was stirred for a further 4 hours at room temperature. To this reaction solution, add 5 ml of cold water to 0 ° C.
After adding and stirring for 30 minutes, 20 ml of 25% aqueous ammonia was added, and the mixture was stirred at 50 ° C. for 2 hours. After concentrating this reaction solution under reduced pressure, it was purified with an ion exchange resin (PK216),
Crystallized from water-ethanol, 2.04 g of target compound
(83.9%) was obtained.
【００１６】実施例２：５−メチルシチジン（式
［Ｉ］、Ｒ1＝ＣＨ3、Ｒ2＝Ｒ4＝Ｈ、Ｒ3＝Ｒ5＝ＯＨ）
の合成 ５-メチルウリジン２５.８ｇのピリジン５００ｍｌ溶
液、ＴＭＳクロリド５１ｍｌ、オキシ塩化リン２０ｍ
ｌ、冷水５０ｍｌ、２５％アンモニア水２００ｍｌを用
い、実施例１と同様に処理して目的化合物１９.０４ｇ
（７４.０％）を得た。Example 2: 5-Methylcytidine (Formula [I], R 1 = CH 3 , R 2 = R 4 = H, R 3 = R 5 = OH)
Synthesis of 2-methyluridine (25.8 g) in pyridine (500 ml), TMS chloride (51 ml), phosphorus oxychloride (20 m)
1, cold water 50 ml, and 25% ammonia water 200 ml were treated in the same manner as in Example 1 to obtain the target compound 19.04 g.
(74.0%) was obtained.
【００１７】実施例３：５−ブロモシチジン（式
［Ｉ］、Ｒ1＝Ｂｒ、Ｒ2＝Ｒ4＝Ｈ、Ｒ3＝Ｒ5＝ＯＨ）
の合成 ５-ブロモウリジン３２．３ｇのピリジン５００ｍｌ溶
液、ＴＭＳクロリド５１ｍｌ、オキシ塩化リン２０ｍ
ｌ、冷水５０ｍｌ、２５％アンモニア水２００ｍｌを用
い、実施例１と同様に処理して目的化合物を合成でき
る。Example 3: 5-Bromocytidine (Formula [I], R 1 = Br, R 2 = R 4 = H, R 3 = R 5 = OH)
Synthesis of 5-bromouridine (32.3 g) in pyridine (500 ml), TMS chloride (51 ml), phosphorus oxychloride (20 m)
Using 1, 1, 50 ml of cold water and 200 ml of 25% ammonia water, the same treatment as in Example 1 can be carried out to synthesize the target compound.
Claims (1)
子を示し、Ｒ2、Ｒ3、Ｒ4およびＲ5は、同一であっても
異なっていてもよく、水素原子または水酸基を示す。）
で表される４−アミノピリミジンヌクレオシドの製造法
であって、式［ＩＩ］ 【化２】 （式中、Ｒ1、Ｒ2、Ｒ3、Ｒ4およびＲ5は前記と同意
義。）で表される４−ヒドロキシピリミジンヌクレオシ
ドの糖部水酸基をトリメチルシリル基で保護した後、オ
キシ塩化リンまたは４−クロロフェニルホスホロジクロ
リデートと反応させ、得られた中間体を単離することな
くアンモニア水と反応させてトリメチルシリル基の除去
と塩基部４位のアミノ化を行い上記式［Ｉ］で表される
４−アミノピリミジンヌクレオシドを得ることを特徴と
する４−アミノピリミジンヌクレオシドの製造法。1. The formula [I]: (In the formula, R 1 represents a hydrogen atom, a lower alkyl group or a halogen atom, and R 2 , R 3 , R 4 and R 5 may be the same or different and represent a hydrogen atom or a hydroxyl group. )
A method for producing a 4-aminopyrimidine nucleoside represented by the formula [II] (In the formula, R 1 , R 2 , R 3 , R 4 and R 5 have the same meanings as described above.) After protecting the sugar group hydroxyl group of 4-hydroxypyrimidine nucleoside with a trimethylsilyl group, phosphorus oxychloride or Reacting with 4-chlorophenylphosphorodichloridate, the resulting intermediate is reacted with aqueous ammonia without isolation to remove the trimethylsilyl group and aminate the 4-position of the base moiety to obtain the compound represented by the above formula [I]. A method for producing 4-aminopyrimidine nucleoside, which comprises obtaining 4-aminopyrimidine nucleoside.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24092795A JPH0959292A (en) | 1995-08-25 | 1995-08-25 | Process for producing 4-aminopyrimidine nucleoside |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24092795A JPH0959292A (en) | 1995-08-25 | 1995-08-25 | Process for producing 4-aminopyrimidine nucleoside |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0959292A true JPH0959292A (en) | 1997-03-04 |
Family
ID=17066721
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP24092795A Pending JPH0959292A (en) | 1995-08-25 | 1995-08-25 | Process for producing 4-aminopyrimidine nucleoside |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0959292A (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7456155B2 (en) | 2002-06-28 | 2008-11-25 | Idenix Pharmaceuticals, Inc. | 2′-C-methyl-3′-O-L-valine ester ribofuranosyl cytidine for treatment of flaviviridae infections |
| US7582618B2 (en) | 2002-06-28 | 2009-09-01 | Idenix Pharmaceuticals, Inc. | 2′-C-methyl-3′-O-L-valine ester ribofuranosyl cytidine for treatment of flaviviridae infections |
| US7595390B2 (en) | 2003-04-28 | 2009-09-29 | Novartis Ag | Industrially scalable nucleoside synthesis |
| US7598373B2 (en) | 2002-12-12 | 2009-10-06 | Idenix Pharmaceuticals, Inc. | Process for the production of 2-C-methyl-D-ribonolactone |
| US7608597B2 (en) | 2000-05-23 | 2009-10-27 | Idenix Pharmaceuticals, Inc. | Methods and compositions for treating hepatitis C virus |
| EP2157095A2 (en) | 2003-06-30 | 2010-02-24 | Novartis Ag | Synthesis of beta-L-2-Deoxy nucleosides |
| US9968628B2 (en) | 2000-05-26 | 2018-05-15 | Idenix Pharmaceuticals Llc | Methods and compositions for treating flaviviruses and pestiviruses |
| US10525072B2 (en) | 2002-11-15 | 2020-01-07 | Idenix Pharmaceuticals Llc | 2′-branched nucleosides and flaviviridae mutation |
| CN113735926A (en) * | 2021-09-14 | 2021-12-03 | 江苏香地化学有限公司 | Synthesis process of uridine |
-
1995
- 1995-08-25 JP JP24092795A patent/JPH0959292A/en active Pending
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7608597B2 (en) | 2000-05-23 | 2009-10-27 | Idenix Pharmaceuticals, Inc. | Methods and compositions for treating hepatitis C virus |
| US10363265B2 (en) | 2000-05-23 | 2019-07-30 | Idenix Pharmaceuticals Llc | Methods and compositions for treating hepatitis C virus |
| US10758557B2 (en) | 2000-05-23 | 2020-09-01 | Idenix Pharmaceuticals Llc | Methods and compositions for treating hepatitis C virus |
| US9968628B2 (en) | 2000-05-26 | 2018-05-15 | Idenix Pharmaceuticals Llc | Methods and compositions for treating flaviviruses and pestiviruses |
| US7456155B2 (en) | 2002-06-28 | 2008-11-25 | Idenix Pharmaceuticals, Inc. | 2′-C-methyl-3′-O-L-valine ester ribofuranosyl cytidine for treatment of flaviviridae infections |
| US7582618B2 (en) | 2002-06-28 | 2009-09-01 | Idenix Pharmaceuticals, Inc. | 2′-C-methyl-3′-O-L-valine ester ribofuranosyl cytidine for treatment of flaviviridae infections |
| US10525072B2 (en) | 2002-11-15 | 2020-01-07 | Idenix Pharmaceuticals Llc | 2′-branched nucleosides and flaviviridae mutation |
| US7598373B2 (en) | 2002-12-12 | 2009-10-06 | Idenix Pharmaceuticals, Inc. | Process for the production of 2-C-methyl-D-ribonolactone |
| US7595390B2 (en) | 2003-04-28 | 2009-09-29 | Novartis Ag | Industrially scalable nucleoside synthesis |
| EP2157095A2 (en) | 2003-06-30 | 2010-02-24 | Novartis Ag | Synthesis of beta-L-2-Deoxy nucleosides |
| CN113735926A (en) * | 2021-09-14 | 2021-12-03 | 江苏香地化学有限公司 | Synthesis process of uridine |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2025028117A (en) | Method for producing nicotinamide ribofuranoside salts, nicotinamide ribofuranoside salts themselves, and uses thereof | |
| JP3653292B2 (en) | Mass production of 2 ', 3'-didehydro-3'-deoxythymidine (d4T) using 5-methyluridine | |
| JP3677790B2 (en) | Nucleoside derivatives and process for producing the same | |
| JP4742868B2 (en) | (2R) -2-Propyloctanoic acid production method and intermediate | |
| JP5563558B2 (en) | Preparation of intermediates useful for the synthesis of 2'-cyano-2'-deoxy-N4-palmitoyl-1-beta-D-arabinofuranosylcytosine | |
| CN1030658C (en) | Octadecyl(2-(N-methyl-priperidino)-ethyl)-phosphate and process for its preparation | |
| JPH09165396A (en) | Production of 1-beta-d-arabinofuranosylcytosine | |
| EP1186612B1 (en) | Process for the preparation of cytidine derivatives | |
| JPH04253993A (en) | Preparation of deoxynucleosides | |
| JPH01143892A (en) | Production of cytosine derivative | |
| BG51252A3 (en) | Method for netylmycin preparation | |
| JPH0931092A (en) | Process for producing 2'-3'-di-O-acyl ATP | |
| US5536824A (en) | Organosulfonyl salts of 2,3'-O-cyclocytidine | |
| JPH10130244A (en) | Method for producing acyclonucleoside | |
| JPH0665281A (en) | Improved preparation of 2-amino(2,3,5-tri-o-benzyl-beta- arabinofuranosyl)adenine | |
| JP3499896B2 (en) | Method for producing 2'-deoxynucleosides | |
| JPS6230998B2 (en) | ||
| CA2012095C (en) | 3'-tosylcytidine compounds and process for production thereof | |
| JPH0570419A (en) | Theanine manufacturing method | |
| JPS59152399A (en) | Preparation of nucleic acid derivative | |
| JPS5930720B2 (en) | Method for producing 5-bromouracil nucleoside | |
| GB2096596A (en) | 8-quinolinesulfonyl derivatives and their synthesis and use as coupling agents in nucleotide chemistry | |
| JPH04505153A (en) | Novel 2'-deoxyribonucleoside derivatives and their applications | |
| JPH02160799A (en) | Preparation of 2'-deoxy-beta-adenosine | |
| JPH0368879B2 (en) |