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Updated: Jul 13, 2026

Metabolic Glycoengineering of Sialic Acid Using N-acyl-modified Mannosamines
Published on: November 25, 2017
An improved synthesis of a key intermediate for (+)-biotin from D-mannose
Fen-Er Chen1, Jian-Feng Zhao, Fang-Jun Xiong
1Fudan-DSM Joint Laboratory for Synthetic Methods and Chiral Technology, Department of Chemistry, Fudan University, Shanghai 200433, People's Republic of China. rfchen@fudan.edu.cn
Abstract:
An efficient and reproducible process for the synthesis of methyl 2,3,4,5-tetradeoxy-7,8-O-isopropylidene-D-arabino-nanonate (2), a key intermediate in the total synthesis of (+)-biotin (1), starting from readily available D-mannose is described. The crucial part of this synthesis was the development of a practical route to a novel O-benzyl protected unsaturated ester methyl (benzyl 5,6,7,8-tetradeoxy-2,3-O-isopropylidene-alpha-D-lyxo-nona-5,7-dienofuranosid) uronate (7), allowing the one-step preparation of hydroxy ester methyl 5,6,7,8-tetradeoxy-2,3-O-isopropylidene-alpha-D-lyxo-nanofuranuronate (8) by the catalytic debenzylation and hydrogenation over palladium on carbon catalyst. This procedure requires no chromatographic purification, which makes it ideal for synthetic preparation on an industrial scale.
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