1597486-93-5Relevant articles and documents
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.
