DD276096A1 - PROCESS FOR THE PREPARATION OF S-GLYCOSIDES - Google Patents
PROCESS FOR THE PREPARATION OF S-GLYCOSIDES Download PDFInfo
- Publication number
- DD276096A1 DD276096A1 DD32046988A DD32046988A DD276096A1 DD 276096 A1 DD276096 A1 DD 276096A1 DD 32046988 A DD32046988 A DD 32046988A DD 32046988 A DD32046988 A DD 32046988A DD 276096 A1 DD276096 A1 DD 276096A1
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- general formula
- glycosides
- preparation
- hydrogen atom
- acetylated
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 6
- 238000002360 preparation method Methods 0.000 title claims abstract description 6
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 229930182475 S-glycoside Natural products 0.000 claims abstract description 5
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 3
- JHIVVAPYMSGYDF-PTQBSOBMSA-N cyclohexanone Chemical class O=[13C]1CCCCC1 JHIVVAPYMSGYDF-PTQBSOBMSA-N 0.000 claims abstract description 3
- 125000002820 allylidene group Chemical group [H]C(=[*])C([H])=C([H])[H] 0.000 abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- SFOZKJGZNOBSHF-RGDJUOJXSA-N [(2r,3r,4s,5r,6s)-3,4,5-triacetyloxy-6-sulfanyloxan-2-yl]methyl acetate Chemical compound CC(=O)OC[C@H]1O[C@@H](S)[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@@H]1OC(C)=O SFOZKJGZNOBSHF-RGDJUOJXSA-N 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000002243 cyclohexanonyl group Chemical class *C1(*)C(=O)C(*)(*)C(*)(*)C(*)(*)C1(*)* 0.000 description 1
- 229960003082 galactose Drugs 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Landscapes
- Saccharide Compounds (AREA)
Abstract
Die Erfindung betrifft ein Verfahren zur Herstellung von S-Glycosiden. Ziel der Erfindung ist es, ein Verfahren fuer die Herstellung von acetylierten 2-&3-Aryl-3-(b-D-glycopyranosylthio)prop-2-enyliden!-6-furfuryliden-cyclohexanonen zu entwickeln. Die S-Glycoside der allgemeinen Formel III, in der R fuer einen gegebenenfalls substituierten Phenylrest und R1, R2 fuer ein Wasserstoffatom (Acetoxygruppe) oder eine Acetoxygruppe (Wasserstoffatom) stehen, koennen durch Umsetzung der Cyclohexanonderivate der allgemeinen Formel I, in der R die obige Bedeutung besitzt, mit acetylierten 1-Thio-b-D-glycopyranosen der allgemeinen Formel II, in der R1 und R2 wie oben definiert sind, in Gegenwart von Basen hergestellt werden.The invention relates to a process for the preparation of S-glycosides. The aim of the invention is to develop a process for the preparation of acetylated 2- & 3-aryl-3- (b-D-glycopyranosylthio) prop-2-enylidene! -6-furfurylidenecyclohexanones. The S-glycosides of the general formula III in which R is an optionally substituted phenyl radical and R 1, R 2 is a hydrogen atom (acetoxy group) or an acetoxy group (hydrogen atom) can be converted by reacting the cyclohexanone derivatives of the general formula I in which R is the above Meaning, with acetylated 1-thio-bD-glycopyranosen of the general formula II, in which R1 and R2 are as defined above, be prepared in the presence of bases.
Description
furfuryliden-cyclohexanonen.furfurylidene cyclohexanones.
verwendet werden.be used.
Aufgabe der Erfindung ist es, auf der Basis der 2-|3-Aryi-3-ch!or-prop-2-enyliden]-6-furfuryliden-cyclohexanone eine Synthese der acatylierten 2-[3-Aryl-3-(ß-D-glycopyr0nosylthlo)prop-2-enyliden)-6-furfuryliden-cyclohexanone zu ermöglichen. Erfindungsgemäß können die S-Glycoside der allgemeinen Formel III, in der R für einen gegebenenfalls substituierten Phenylrest und R', R' für ein Wasserstoffatom (Acetoxygruppe) oder eine Acetoxygruppe (Wasserstoffatom) stehen, durch Umsetzung der Cyclohexanonderivate der allgemeinen Formel I, in der R die obige Bedeutung besitzt mit acetylierten 1-Thlo-ß-D-glycopyranosen der allgemeinen Formel II, In der R1 und R2 wie obon definiert sind, in Gegenwart von Basen hergestellt werden. Die Umsetzungen werden in organischen Lösungsmitteln, vorzugsweise in Dimethylformamid, in Gegenwart einer Base, vorzugsweise Kaliumcarbonat, vorgenommen. Die Reaktionstemperaturen reichen von 10 bis 50*C. In Abhängigkeit von diesen Reaktionstemperaturen betragen die Reaktionszeiten 30 Minuten bis zu 5 Stunden. Es Ist zweckmäßig, die Reaktionsmischungen zu rühren, wenn eine in dem Lösungsmittel nicht vollständig lösliche Base verwendet wird. Die Aufarbeitung der Reaktionsansätze erfolgt durch Versetzen mit Wasser und Ansäuern mit verdünnter Mineralsäure. Dabei fallen sirupösa Produkte an, die nach dem Waschen mit Wasser aus organischen Lösungsmitteln zur weiteren Reinigung umkristallisiert werden.The object of the invention is, based on the 2- | 3-Aryi-3-ch! Or-prop-2-enyliden] -6-furfurylidenecyclohexanone a synthesis of acatylated 2- [3-aryl-3- (ß -D-glycopyr0nosylthlo) prop-2-enylidene) -6-furfurylidenecyclohexanone. According to the invention, the S-glycosides of the general formula III, in which R is an optionally substituted phenyl radical and R ', R' is a hydrogen atom (acetoxy group) or an acetoxy group (hydrogen atom), can be prepared by reacting the cyclohexanone derivatives of the general formula I, in R has the above meaning with acetylated 1-THLO-ß-D-glycopyranoses of the general formula II in which R 1 and R 2 are as obon are defined, in the presence of bases. The reactions are carried out in organic solvents, preferably in dimethylformamide, in the presence of a base, preferably potassium carbonate. The reaction temperatures range from 10 to 50 ° C. Depending on these reaction temperatures, the reaction times are 30 minutes to 5 hours. It is expedient to stir the reaction mixtures if a base which is not completely soluble in the solvent is used. The work-up of the reaction mixtures is carried out by addition of water and acidification with dilute mineral acid. These are syrupösa products, which are recrystallized after washing with water from organic solvents for further purification.
2-[3-(2,3,4,6-Tetra-0-acetyl-P-D-glucopyranosylthio)-3-phenyl-prop-2-enyliden]-6-furfuryliden-cyclohexanon2- [3- (2,3,4,6-tetra-0-acetyl-P-D-glucopyranosylthio) -3-phenyl-prop-2-enylidene] -6-Furfurylidene-cyclohexanone
2,3,4,6-Tetra-0-acetyl-1-thio-ß-D-glucopyranose, 2g Kaliumcarbonat und 10ml Dimethylformamid 2 Stunden bei 24'C. Die2,3,4,6-Tetra-O-acetyl-1-thio-β-D-glucopyranose, 2g potassium carbonate and 10ml dimethylformamide for 2 hours at 24'C. The
in heißem Ethanol aufgenommen wird. Man läßt die ethanolische Lösung zur Kristallisation bei Raumtemperatur stehen, filtriert den Niederschlag ab, wäscht diesen mit wenig Ethanol und kristallisiert ihn aus Ethanol um.is taken up in hot ethanol. The ethanolic solution is allowed to crystallize at room temperature, the precipitate is filtered off, washed with a little ethanol and recrystallized from ethanol.
0,01 mol/mol 2·(3·ΟηΙθΓ·3·ρηβηνΙ·ρΓθρ·2·θηνΙΙαοη)·6·ίυΓΚ^ΙΙαοη-ονοΙοηβχ3ηοη, 0,01 mol/mol 2,3,4,ο·ΤβΚβ·0·80βΙνΙ·ΜΙι1ο·β·Ο· galactopyranose und 2g Kaliumcarbonat werdon umgosotzt, wie unter Au&führungsbelsplol 1 beschrieben. Ausbeute: 47% d. Th. Schmelzpunkt:0.01 mol / mol 2 · (3 · ΟηΙθΓ · 3 · ρηβηνΙ · ρΓθρ · 2 · θηνΙΙαοη) · 6 · ΓΚυΓΚ ^ ΙΙαοη-ονοΙοηβχ3ηοη, 0.01 mol / mol 2,3,4, ο · ΤβΚβ · 0 · 80βΙνΙ · ΜΙι1ο · β · Ο · galactopyranose and 2g potassium carbonate are grafted as described under Au & Führungbelsplol 1. Yield: 47% d. Th. Melting point:
IOH-OH=O(R)Ol +IOH-OH = O (R) Ol +
OH2OAcOH 2 OAc
OAcOAc
,0Ac, 0AC
S-O(R)=OH-OH=S-O (R) = OH = OH
OAcOAc
III Ac a AcetylIII Ac a Acetyl
' :Π ·Ρ if .'.'' f-!iir J': Π · Ρ if.'. '' F - ! ii r J
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD32046988A DD276096A1 (en) | 1988-10-05 | 1988-10-05 | PROCESS FOR THE PREPARATION OF S-GLYCOSIDES |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD32046988A DD276096A1 (en) | 1988-10-05 | 1988-10-05 | PROCESS FOR THE PREPARATION OF S-GLYCOSIDES |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD276096A1 true DD276096A1 (en) | 1990-02-14 |
Family
ID=5602954
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD32046988A DD276096A1 (en) | 1988-10-05 | 1988-10-05 | PROCESS FOR THE PREPARATION OF S-GLYCOSIDES |
Country Status (1)
| Country | Link |
|---|---|
| DD (1) | DD276096A1 (en) |
-
1988
- 1988-10-05 DD DD32046988A patent/DD276096A1/en not_active IP Right Cessation
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