2’-氯乙基-β-D-葡萄糖苷的合成.pdfVIP

Scientific Journal of Frontier Chemical Development March 2014, Volume 4, Issue 1, PP.6-13 Synthesis of 2’-Chloroethyl β-D- Glucopyranoside Na Kuang, Dengfen Liu, Langqiu Chen# College of Chemistry, Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, Xiangtan University, Xiangtan 411105, China #Email: chengood2003@263.net Abstract 2’-Chloroethyl 2, 3, 4, 6-tetra-O-acetyl-β-D-glucopyranoside (5) and 2’-chloroethyl β-D-glucopyranoside (6) are potent intermediates for carbohydrate drug synthesis. With D-glucose (1) as a raw material, a corresponding 2, 3, 4, 6-tetra-O-acetyl-D- glucopyranosyl trichloroacetamide (2) was prepared through acetylation, deacetylation at C1 postion, reacting with trichloroacetinitrile. With the ester as a donor, coupling reaction with 2-chloroethanol was taken at the catalysis of BF ∙Et O to an 3 2 1, 2-trans compound 2’-chloroethyl 2, 3, 4, 6-tetra-O-acetyl-β-D-glucopyranoside (5). The latter was deacetylated to obtain 2’- chloroethyl β-D-glucopyranoside (6). The synthetical routine is rational and practical. Keywords: 2’-Chloroethyl 2, 3, 4, 6-tetra-O-acetyl-β-D-glucopyranoside; 2’-Chloroethyl β-D-glucopyranoside; D-glucose; 2- Chloroethanol; Synthesis 2’-氯乙基-β-D-葡萄糖苷的合成* 旷娜，刘灯峰，陈朗秋 湘潭大学化学学院环境友好化学与应用省部共建教育部重点实验室，湖南省湘潭市411105 摘 要：2’-氯乙基-2,3,4,6- 四-O- 乙酰基-β-D- 吡喃葡萄糖苷（5）和2’-氯乙基-β-D- 吡喃葡萄糖苷（6）是潜在的糖类药物 合成的中间体。以D-葡萄糖（1）为原料，通过乙酰化、C1 位选择性脱乙酰基、与三氯乙腈反应，转变成相应的 2,3,4,6- 四-O- 乙酰基-D- 吡喃葡萄糖基三氯乙酰亚胺酯（4 ）。以该酯为供体，在三氟化硼乙醚催化下与 2-氯乙醇偶联，得到了 1,2-反式结构的 2’-氯乙基-2,3,4,6- 四-O- 乙酰基-β-D- 吡喃葡萄糖苷（5）。后者脱去乙酰基保护，获得了 2’-氯乙基-β-