使用氟代保护基的快速寡糖合成

Rapid oligosaccharide synthesis using a fluorous protective group.

作者信息

Miura Tsuyoshi, Goto Kohtaro, Waragai Hideki, Matsumoto Hiroharu, Hirose Yuriko, Ohmae Masashi, Ishida Hide-Ki, Satoh Ai, Inazu Toshiyuki

机构信息

The Noguchi Institute, 1-8-1 Kaga, Itabashi-ku, Tokyo 173-0003, Japan.

出版信息

J Org Chem. 2004 Aug 6;69(16):5348-53. doi: 10.1021/jo049425k.

DOI:10.1021/jo049425k

PMID:15287781

Abstract

The Bfp-OH, a novel fluorous protecting reagent, was able to be easily prepared. The Bfp group was readily introduced to a carbohydrate, removed in high yield, and recyclable after cleavage. The use of the Bfp group made it possible to synthesize a pentasaccharide by minimal column chromatography purification. Each synthetic intermediate was able to be easily purified only by simple fluorous-organic solvent extraction and monitored by TLC, NMR, and MS.

摘要

新型氟代保护试剂Bfp-OH易于制备。Bfp基团可轻松引入到碳水化合物中，以高产率去除，且裂解后可回收利用。使用Bfp基团使得通过最少的柱色谱纯化来合成五糖成为可能。每个合成中间体仅通过简单的氟代有机溶剂萃取就能轻松纯化，并通过薄层色谱、核磁共振和质谱进行监测。