2124-57-4Relevant articles and documents
PROCESS OF VITAMIN K2 DERIVATIVES PREPARATION
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, (2021/04/17)
The invention relates to an improved process of vitamin K2 derivatives preparation via the alkylation of the menadione-cyclopentadiene adduct.
Menaquinol Compositions and Methods of Treatment
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, (2020/04/09)
The present application discloses methods for the efficient preparation of high purity compounds of the Formula I, and their methods of use.
PROCESS OF VITAMIN K2 DERIVATIVES PREPARATION
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, (2019/10/29)
Provided is an improved process of vitamin K2 derivatives preparation, represented by formula (I) wherein n is an integer from 3 to 13.
Convergent Synthesis of Menaquinone-7 (MK-7)
Baj, Aneta,Wa?ejko, Piotr,Kutner, Andrzej,Kaczmarek, ?ukasz,Morzycki, Jacek W.,Witkowski, Stanis?aw
, p. 1026 - 1033 (2016/11/11)
A practical synthesis of menaquinone-7 (MK-7, Vitamin K2) in the all-trans form was designed. Stereoselective synthesis of MK-7 was achieved through a "1 + 6" convergent strategy by condensation of two building blocks, menadione monoprenyl derivative (fragment "1") with hexaprenyl bromide (fragment "6", 82%). Pd-catalyzed desulfonation with LiEt3BH (78%) was followed by oxidation of the hydroquinone moiety using ammonium cerium(IV) nitrate (72%). The major challenge in our methodology was the preparation of all-trans hexaprenyl bromide by coupling of two triprenyl units derived from trans, trans-farnesol. Manufacturing on a pilot scale was accomplished through our approach. The scalable method was designed especially for a large, kilogram-scale production from easily available intermediates. Furthermore, the proposed methodology avoids many chromatographic purifications and allows for a relatively cost-effective manufacturing. Moreover, our synthesis yielded high-purity (99.9%) final product MK-7, which can be used as a dietary supplement as well as an active pharmaceutical ingredient.
Convergent synthesis of menaquinone-7 (MK-7)
Baj, Aneta,Wa?ejko, Piotr,Kutner, Andrzej,Kaczmarek, L?ukasz,Morzycki, Jacek W,Witkowski, Stanisl?aw
, p. 1026 - 1033 (2017/01/16)
A practical synthesis of menaquinone-7 (MK-7, vitamin K2) in the all-Trans form was designed. Stereoselective synthesis of MK-7 was achieved through a "1 + 6" convergent strategy by condensation of two building blocks, menadione monoprenyl derivative (fragment "1") with hexaprenyl bromide (fragment "6", 82%). Pd-catalyzed desulfonation with LiEt3BH (78%) was followed by oxidation of the hydroquinone moiety using ammonium cerium(IV) nitrate (72%). The major challenge in our methodology was the preparation of all-Trans hexaprenyl bromide by coupling of two triprenyl units derived from trans,trans-farnesol. Manufacturing on a pilot scale was accomplished through our approach. The scalable method was designed especially for a large, kilogram-scale production from easily available intermediates. Furthermore, the proposed methodology avoids many chromatographic purifications and allows for a relatively cost-effective manufacturing. Moreover, our synthesis yielded high-purity (99.9%) final product MK-7, which can be used as a dietary supplement as well as an active pharmaceutical ingredient.
Method of preparation of stereospecific quinone derivatives
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, (2015/05/19)
A novel process for the regio- and stereospecific synthesis of polyprenylated quinone derivatives, such as Vitamin K1, K2 and Ubiquinone, has been achieved exploiting dithioacetal-, especially 1,3-dithiane-, mediated Umpolung chemistry which works along a new concept "Inhibiting resonance delocalization (IRD)" to overcome isomerization generated due to delocalization of allylic carbanions on the π-electron cloud of an allylic system. The present novel synthesis of all-trans Vitamins K1, K2 and Ubiquinone is achieved by coupling of a quinone group with a polyprenyl side chain where either of the two moieties may have 1,3-dithiane as a terminal group while undergoing umpolung chemistry. Similarly while coupling two polyprenyl fragments to each other in building of the all-trans side chain. A stereospecific synthesis of vitamin K1 was also achieved along the same synthetic outline using a chiral hexahydrofarnesyl derivative retaining optical and geometrical isomeric properties equivalent to those of the natural K1.
METHOD OF PREPARATION OF STEREOSPECIFIC QUINONE DERIVATIVES
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, (2015/05/13)
The description provides processes for the regio and stereospecific synthesis of polyprenylatedquinone derivatives, such as Vitamin K1, K2 and Ubiquinone, exploiting dithioacetals, especially 1,3-dithiane, mediated Umpolung chemistry which works along a new concept “Inhibiting resonance delocalization (IRD)” to overcome isomerization generated due to delocalization of allyliccarbanion on the π-electron cloud of an allylic systems by the conventional synthesis.
PROCESS FOR PREPARATION OF MK-7 TYPE OF VITAMIN K2
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, (2014/05/07)
Process for preparation of MK-7 type of vitamin K2 is characterized by attaching hexaprenyl chain of ?all-trans" configuration to monoprenyl derivative of menadiol following ?1 + 6" synthetic strategy. According to the invention, a-sulfonyl carbanion generated in situ from the protected monoprenyl menadiol of the formula (II), wherein R1 represents C1-3-alkyl group, is reacted with hexaprenyl halide of the formula (VII), wherein X represents halogen atom, preferably bromine, both Z' and Z' represent H or one of Z' and Z" represents H and the other represents phenylsulfonyl group -SO2Ph in the alkylation reaction. The hexaprenyl halide of formula (VII) is obtained by coupling two triprenyl units in alkylation reaction, with or without separation of the intermediates.
