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- Title
Direct C5-Isomerization Approach to l-Iduronic Acid Derivatives.
- Authors
Cao, XuefENg; Lv, Qingqing; Li, Dongmei; Ye, Hui; Yan, Xu; Yang, Xiande; Gan, Hao; Zhao, Wei; Jin, Lan; Wang, PENg; ShEN, Jie
- Abstract
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.
- Subjects
ISOMERIZATION; ACID derivatives; EPIMERIZATION; CARBOHYDRATES; SULFATES
- Publication
Asian Journal of Organic Chemistry, 2015, Vol 4, Issue 9, p899
- ISSN
2193-5807
- Publication type
Article
- DOI
10.1002/ajoc.201500269