半乳凝素-3潜在抑制剂—1-O-烯丙基-4-O-{3-脱氧-3-[4-苄胺羰基-1H-（1，2，3）三氮唑-1-基]-β-D-吡喃半乳糖基}-2-脱氧-2-乙酰氨基-β-D-吡喃葡萄糖的合成

以乳糖为原料设计合成了半乳凝素-3的潜在抑制剂—1-O-烯丙基-4-O-{3-脱氧-3-4-苄胺羰基-1H-（1,2,3）三氮唑-1-基]-β-D-吡喃半乳糖基}-2-脱氧-2-乙酰氨基-β-D-吡喃葡萄糖。乳糖2-位的改造采用了叠氮-碘糖基化法,在乙酰氨基引入的同时立体选择性地构建了β-氨基乳糖苷;通过两次构型翻转在3′-位引入叠氮基,然后采用Click反应构建出三氮唑羧基,再与苄胺反应便得到目标物。对乳糖的上述改造旨在提高其对半乳凝素-3的亲和活性。

Synthesis of allyl 4-O-{3-deoxy-3-[4-benzylaminocarbonyl- 1H-(1,2,3)-triazol-1-yl]-β-D-galactopyranosyl}-2-deoxy-2-acetamido-β-D-glucopyranoside as a potential inhibitor of galectin-3

Allyl 4-O-{3-deoxy-3-4-benzylaminocarbonyl-1H-（1,2,3）-triazol-1-yl]-β-D-galactopyranosyl}-2-deoxy-2-acetamido- β-D-glucopyranoside, a potential inhibitor of galectin-3, was designed and synthesized using lactose as stating material. The modifications of lactose included in introducing of N-acetamino group at the C-2 position through an azidoiodoglycosylation meanwhile constructing the 3-aminolactoside stereoselectively and replacing 3＇-OH with substituent 1,2,3-triazolyl group to enhance the affinity toward galeetin-3.