羟基肉桂酰化的α-L-阿拉伯呋喃糖基-(1→2)-和(1→3)-β-D-木吡喃糖苷的合成与光谱表征

Synthesis and spectroscopic characterization of hydroxycinnamoylated methyl alpha-L-arabinofuranosyl-(1-->2)- and (1-->3)-beta-D-xylopyranosides.

作者信息

Helm R F, Ralph J

机构信息

USDA-Agricultural Research Service, US Dairy Forage Research Center, Madison, WI 53706.

出版信息

Carbohydr Res. 1993 Feb 24;240:23-38. doi: 10.1016/0008-6215(93)84168-6.

DOI:10.1016/0008-6215(93)84168-6

PMID:8458010

Abstract

A reaction sequence for the preparation of methyl 5-O-feruloyl-alpha-L- arabinofuranosyl-(1-->3)-beta-D-xylopyranoside, the companion 5-O-p-coumaroyl disaccharide, and their (1-->2) analogs has been developed. The (1-->3) hydroxycinnamoylated disaccharides are available in 11 steps from L-arabinose and methyl beta-D-xylopyranoside in 17% overall yield (based on methyl beta-D-xylopyranoside). The corresponding (1-->2) materials were prepared in 9 steps in > 37% overall yield. Complete spectral characterization provides unambiguous assignments for comparison with analogous materials isolated from plant cell-walls. Conformational aspects of the prepared materials are discussed in relation to coupling-constant information.

摘要

已开发出一条用于制备5-O-阿魏酰基-α-L-阿拉伯呋喃糖基-(1→3)-β-D-木吡喃糖苷、其对应的5-O-对香豆酰基二糖及其(1→2)类似物的反应序列。从L-阿拉伯糖和β-D-木吡喃糖苷出发，经过11步反应可得到(1→3)羟基肉桂酰化二糖，总产率为17%（基于β-D-木吡喃糖苷）。相应的(1→2)产物经过9步反应制备得到，总产率>37%。完整的光谱表征为与从植物细胞壁分离得到的类似物质进行比较提供了明确的归属。根据耦合常数信息讨论了所制备物质的构象方面。