2-脱氧-D-核糖呋喃糖的氮杂类似物及其同系物的合成。

Synthesis of an aza analogue of 2-deoxy-D-ribofuranose and its homologues.

作者信息

Filichev V V, Brandt M, Pedersen E B

机构信息

Department of Chemistry, University of Southern Denmark, Odense University, DK-5230 Odense M, Denmark.

出版信息

Carbohydr Res. 2001 Jul 3;333(2):115-22. doi: 10.1016/s0008-6215(01)00132-x.

DOI:10.1016/s0008-6215(01)00132-x

PMID:11448671

Abstract

Azasugars were obtained in one-pot reactions by catalytic reduction reactions of amino group precursors in aldosugars followed by intramolecular reductive amino alkylation reactions. (3R,4S)-4-[(1S)-1,2-Dihydroxyethyl]pyrrolidin-3-ol was obtained from D-xylose by two different strategies through 3-C-cyano-3-deoxy-D-ribo-pentofuranose or 3-C-azidomethyl-3-deoxy-D-ribo-pentofuranose in 6 and 16% overall yields, respectively. The oxidative cleavage of the diol group in the corresponding Fmoc-azasugar followed by deprotection afforded (3R,4R)-4-(hydroxymethyl)pyrrolidin-3-ol. (3R,4S)-4-[(1S,2R)-1,2,3-Trihydroxypropyl]pyrrolidin-3-ol was synthesized from diacetone-D-glucose through 3-deoxy-3-C-nitromethyl-D-allose and the overall yield was 7%.

摘要

氮杂糖是通过醛糖中氨基前体的催化还原反应，随后进行分子内还原氨基烷基化反应，在一锅反应中获得的。(3R,4S)-4-[(1S)-1,2-二羟基乙基]吡咯烷-3-醇是由D-木糖通过两种不同策略分别经3-C-氰基-3-脱氧-D-核糖戊呋喃糖或3-C-叠氮甲基-3-脱氧-D-核糖戊呋喃糖得到的，总产率分别为6%和16%。相应的Fmoc-氮杂糖中二醇基团的氧化裂解，随后脱保护得到(3R,4R)-4-(羟甲基)吡咯烷-3-醇。(3R,4S)-4-[(1S,2R)-1,2,3-三羟基丙基]吡咯烷-3-醇是由双丙酮-D-葡萄糖经3-脱氧-3-C-硝基甲基-D-阿洛糖合成的，总产率为7%。