PL424875A1 - Method for synthesis of vitamin K2 - Google Patents
Method for synthesis of vitamin K2Info
- Publication number
- PL424875A1 PL424875A1 PL424875A PL42487518A PL424875A1 PL 424875 A1 PL424875 A1 PL 424875A1 PL 424875 A PL424875 A PL 424875A PL 42487518 A PL42487518 A PL 42487518A PL 424875 A1 PL424875 A1 PL 424875A1
- Authority
- PL
- Poland
- Prior art keywords
- compound
- formula
- group
- reaction
- viii
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 4
- 235000019143 vitamin K2 Nutrition 0.000 title abstract 3
- 239000011728 vitamin K2 Substances 0.000 title abstract 3
- PFRQBZFETXBLTP-UHFFFAOYSA-N Vitamin K2 Natural products C1=CC=C2C(=O)C(CC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)CCC=C(C)C)=C(C)C(=O)C2=C1 PFRQBZFETXBLTP-UHFFFAOYSA-N 0.000 title abstract 2
- DKHGMERMDICWDU-GHDNBGIDSA-N menaquinone-4 Chemical compound C1=CC=C2C(=O)C(C/C=C(C)/CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)=C(C)C(=O)C2=C1 DKHGMERMDICWDU-GHDNBGIDSA-N 0.000 title abstract 2
- 230000015572 biosynthetic process Effects 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 10
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- HYPYXGZDOYTYDR-HAJWAVTHSA-N 2-methyl-3-[(2e,6e,10e,14e)-3,7,11,15,19-pentamethylicosa-2,6,10,14,18-pentaenyl]naphthalene-1,4-dione Chemical compound C1=CC=C2C(=O)C(C/C=C(C)/CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)=C(C)C(=O)C2=C1 HYPYXGZDOYTYDR-HAJWAVTHSA-N 0.000 abstract 1
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 abstract 1
- 239000005792 Geraniol Substances 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 238000005869 desulfonation reaction Methods 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 229940113087 geraniol Drugs 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- -1 isoprenyl side chain Chemical group 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000006239 protecting group Chemical group 0.000 abstract 1
- 230000002829 reductive effect Effects 0.000 abstract 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- 229940041603 vitamin k 3 Drugs 0.000 abstract 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Przedmiotem zgłoszenia jest sposób syntezy witaminy K2, w którym do budowy izoprenylowego łańcucha bocznego wykorzystuje się geraniol lub jego pochodną. Sposób charakteryzuje się tym, że sposób obejmuje następujące etapy: a) co najmniej pojedynczą reakcję typu Biellmanna pochodnej (II) ze związkiem o wzorze (III) lub związkiem o wzorze (IV) gdzie m=1 lub m=2, przy czym G' oznacza grupę opuszczającą, Z i Z' oznacza naprzemiennie atom wodoru albo grupę sulfonową; b) usunięcie ze związku (IV) grupy zabezpieczającej PG i substytucję otrzymanej grupy hydroksylowej grupą opuszczającą LG otrzymując związek o wzorze (VIII), w którym n wynosi od 1 do 7; c) reakcję związku (VIII) ze związkiem o wzorze (VII) gdzie R oznacza grupę metylową lub etylową, otrzymując związek o wzorze (IX); d) reakcję reduktywnej desulfonacji związku o wzorze (IX) w celu otrzymania związku o wzorze (X); e) przekształcenie w wyniku reakcji związku o wzorze (X) w menachinon o wzorze (VI).The subject of the application is a method of synthesizing vitamin K2, in which geraniol or a derivative thereof is used to build an isoprenyl side chain. The method is characterized in that the process comprises the following steps: a) at least a single Biellmann-type reaction of derivative (II) with a compound of formula (III) or a compound of formula (IV) where m = 1 or m = 2, with G ' represents a leaving group, Z and Z 'are alternately hydrogen or a sulfo group; b) removing the protecting group PG from the compound (IV) and substituting the resulting hydroxyl group with the leaving group LG to obtain a compound of formula (VIII) wherein n is from 1 to 7; c) reacting a compound of formula (VIII) with a compound of formula (VII) wherein R is a methyl or ethyl group to obtain a compound of formula (IX); d) reductive desulfonation reaction of a compound of formula (IX) to obtain a compound of formula (X); e) converting a compound of formula (X) to a menaquinone of formula (VI) by reaction.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL424875A PL424875A1 (en) | 2018-03-12 | 2018-03-12 | Method for synthesis of vitamin K2 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL424875A PL424875A1 (en) | 2018-03-12 | 2018-03-12 | Method for synthesis of vitamin K2 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL424875A1 true PL424875A1 (en) | 2019-09-23 |
Family
ID=67979645
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL424875A PL424875A1 (en) | 2018-03-12 | 2018-03-12 | Method for synthesis of vitamin K2 |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL424875A1 (en) |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010035000A1 (en) * | 2008-09-24 | 2010-04-01 | Kappa Bioscience As | Process for the preparation of vitamin k2 |
| WO2011117324A2 (en) * | 2010-03-23 | 2011-09-29 | Kappa Bioscience As | Process for the preparation of vitamin k2 |
| PL401195A1 (en) * | 2012-10-12 | 2014-04-14 | Instytut Farmaceutyczny | Process for the preparation of vitamin K2 in the form of MK-7 |
-
2018
- 2018-03-12 PL PL424875A patent/PL424875A1/en unknown
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2010035000A1 (en) * | 2008-09-24 | 2010-04-01 | Kappa Bioscience As | Process for the preparation of vitamin k2 |
| GB2463981A (en) * | 2008-09-24 | 2010-04-07 | Syntavit As | Processes for the preparation of Vitamin K2 derivatives |
| WO2011117324A2 (en) * | 2010-03-23 | 2011-09-29 | Kappa Bioscience As | Process for the preparation of vitamin k2 |
| PL401195A1 (en) * | 2012-10-12 | 2014-04-14 | Instytut Farmaceutyczny | Process for the preparation of vitamin K2 in the form of MK-7 |
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