PL424875A1 - Method for synthesis of vitamin K2 - Google Patents

Method for synthesis of vitamin K2

Info

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
Application number
PL424875A
Other languages
Polish (pl)
Inventor
Piotr Jandziak
Andrzej KRUKOWSKI
Original Assignee
Vitasynth Spółka Z Ograniczoną Odpowiedzialnością
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Vitasynth Spółka Z Ograniczoną Odpowiedzialnością filed Critical Vitasynth Spółka Z Ograniczoną Odpowiedzialnością
Priority to PL424875A priority Critical patent/PL424875A1/en
Publication of PL424875A1 publication Critical patent/PL424875A1/en

Links

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

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.

PL424875A 2018-03-12 2018-03-12 Method for synthesis of vitamin K2 PL424875A1 (en)

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)

* Cited by examiner, † Cited by third party
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

Patent Citations (4)

* Cited by examiner, † Cited by third party
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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