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Direct C5‐Isomerization Approach to l ‐Iduronic Acid Derivatives
Author(s) -
Cao Xuefeng,
Lv Qingqing,
Li Dongmei,
Ye Hui,
Yan Xu,
Yang Xiande,
Gan Hao,
Zhao Wei,
Jin Lan,
Wang Peng,
Shen Jie
Publication year - 2015
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201500269
Subject(s) - iduronic acid , chemistry , epimer , isomerization , synthon , glucuronic acid , stereochemistry , intramolecular force , organic chemistry , catalysis , polysaccharide
Inspired by the biosynthesis of heparan sulfate (HS), we present a direct epimerization approach to l ‐iduronic acid synthons (IdoA) from the corresponding C5 epimers, d ‐glucuronic acids (GlcA). With the best result, 95 % conversion was achieved. Weak intramolecular interactions dramatically affect the equilibrium constants of this thermodynamically governed process. Based on this approach, GlcA and IdoA donors required for the synthesis of fondaparinux were prepared in 14 steps, whereas over 20 steps were required previously.