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报道2条反应条件温和、高效、实用的实验室合成对氯代醌基碳糖苷化合物的路线:其一路线是以芳香碳糖苷1a(1b)为起始原料,在硝酸铵催化下,与N-氯代丁二酰亚胺(NCS)反应获得对氯代芳香碳苷2a(2b),经硝酸铈铵(CAN)脱甲基氧化,得到氯代醌基糖苷3a(3b),总收率为88%(84%);另一路线是通过三甲基氯硅烷在三氟化硼.乙醚作用下对苯醌碳苷4a(4b)的催化加成和水解反应,获得对氯代氢醌基碳苷5a(5b),总收率为82%(76%),而且5a(5b)与氯代醌基糖苷3a(3b)可以通过氧化与还原反应相互转化。
Reported two mild, efficient and practical laboratory conditions for the synthesis of chloroquinone-based carbon glycoside compounds: the first route is based on the aromatic carbon glycoside 1a (1b) as the starting material, ammonium nitrate catalyst, and N -chlorosuccinimide (NCS) to give p-chloronaphthenoside 2a (2b) which is demethylated with cerium ammonium nitrate (CAN) to give chloro-quinone glycoside 3a (3b) Was 88% (84%). The other route was the catalytic addition and hydrolysis of p-benzoquinone carbon glycoside 4a (4b) by trimethylchlorosilane in the presence of boron trifluoride etherate to obtain p-chloro hydroquinone The total yield of Cigosaccharides 5a (5b) was 82% (76%), and 5a (5b) and chloroquinoyl glucoside 3a (3b) were interconverted by oxidation and reduction reactions.