TOTAL SYNTHESIS OF 2,6-DIDEOXY-2,6-IMINO-7-O-BETA-D-GLUCOPYRANOSYL-D-GLYCERO-L-GULO-HEPTITOL HYDROCHLORIDE - A POTENT INHIBITOR OF ALPHA-GLUCOSIDASES
TOTAL SYNTHESIS OF 2,6-DIDEOXY-2,6-IMINO-7-O-BETA-D-GLUCOPYRANOSYL-D-GLYCERO-L-GULO-HEPTITOL HYDROCHLORIDE - A POTENT INHIBITOR OF ALPHA-GLUCOSIDASES
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DOI：
10.1021/jo00230a012
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发表时间：
1987-10-16
影响因子：
3.6
通讯作者：
LIU, PS
中科院分区：
文献类型：
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作者：
LIU, PS
已经合成了2，6-二脱氧-2，6-亚氨基-7-O-β-D-吡喃葡萄糖基-D-甘油-L-古洛-庚糖醇盐酸盐(8)，它是α-葡萄糖苷酶的有效抑制剂。 C1 处的同系化与 2,3,4,6-四-O-苄基-D-吡喃葡萄糖 (1) 的 C5 处的胺化相结合，得到受保护的胺 4。在乙酸汞的催化下，化合物 4 的立体定向分子内环化构成了反应顺序的关键步骤。苷元 6 与乙酰溴葡萄糖进行糖基化，脱保护后产生目标葡萄糖苷 8。
2,6-Dideoxy-2,6-imino-7-O-.beta.-D-glucopyranosyl-D-glycero-L-gulo-heptitol hydrochloride (8), a potent inhibitor of .alpha.-glucosidases, has been synthesized. Homologation at C1 coupled with amination at C5 of 2,3,4,6-tetra-O-benzyl-D-glucopyranose (1) furnished the protected amine 4. A stereospecific intramolecular cyclization of compound 4, catalyzed by mercuric acetate, constituted the key step of the reaction sequence. Glycosylation of the aglycon 6 with acetobromoglucose yielded, after deprotection, the target glucoside 8.