6-脱氧-α-d-艾杜庚糖吡喃基羧酸的合成

Synthesis of 6-deoxy-α-d-ido-heptopyranosyl carboxylic acid

目的对6-脱氧-α-d-艾杜庚糖吡喃基羧酸进行合成研究,以期解决6-脱氧-d-艾杜庚糖类化合物的来源问题。方法通过2-萘甲基的选择性脱除、烯烃的氧化断裂及羟甲基氧化等关键反应操作,完成目标化合物的合成。结果以简便易得的4,6-O-苯亚甲基-α-d-吡喃葡萄糖烯丙基碳苷为原料,经9步反应,以10.2%的总收率合成了6-脱氧-α-d-艾杜庚糖吡喃基羧酸,为6-脱氧-d-艾杜庚糖砌块的合成提供了方法学基础。

Objective The synthesis research on 6-deoxy-α-d-ido-heptopyranosyl carboxylic acid was conducted in order to resolve the problem of the limited sources of 6-deoxy-d-ido-heptopyranose.Methods Selective removal of the 2-naphthylmethyl group,oxidative cleavage of alkene and oxidation of hydroxymethyl were used for the synthesis of the target molecule.Results 6-deoxy-α-d-ido-heptopyranosyl carboxylic acid was synthesized in 9 steps and overall 10.2%yield from 1-C-allyl-α-d-glucopyranoside,laying the solid foundation for the synthesis of 6-deoxy-d-ido-heptopyranose building blocks.