1597487-01-8

Basic information

• Product Name: C₃₈H₅₆O₄S
• Synonyms: C₃₈H₅₆O₄S
• CAS NO: 1597487-01-8
• Molecular Weight: 608.926
• Mol File: 1597487-01-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: C₃₈H₅₆O₄S(CAS DataBase Reference)
• NIST Chemistry Reference: C₃₈H₅₆O₄S(1597487-01-8)
• EPA Substance Registry System: C₃₈H₅₆O₄S(1597487-01-8)

Safety Data

• Hazardous Substances Data: 1597487-01-8(Hazardous Substances Data)

Upstream product

• 106-28-5 Farnesol 
• 40266-21-5 (2E,6E,10E)-3,7,11-trimethyl-12-oxododeca-2,6,10-trien-1-yl acetate 
• 104423-44-1 (2E,6E,10E)-12-bromo-3,7,11-trimethyl-2,6,10-dodecatrienyl acetate 
• 24163-93-7 farnesyl bromide 
• 1597486-72-0 (2E,6E,10E)-3,7,11-trimethyl-12-(phenylsulfonyl)-dodeca-2,6,10-trien-1-yl acetate 
• 4128-17-0 (2E,6E)-farnesyl acetate 

Downstream Products

• 1597486-86-6 phenylsulfonyl hexaprenyl bromide 
• 1597486-87-7 C₆₂H₈₂O₆S₂ 
• 2124-57-4 menaquinone-7 
• 1597486-91-3 C₅₆H₇₈O₄S 

Relevant articles and documents

Convergent Synthesis of Menaquinone-7 (MK-7)

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.

PROCESS FOR PREPARATION OF MK-7 TYPE OF VITAMIN K2

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.