天然产物 6-脱氧-6氨基葡萄糖甘油糖脂的合成

天然氨基甘油糖脂sn-1,2-dipalmitoyl-3-(N-palmitoyl-6-dehydroxy-6-amino-α-glucosyl)glycerol 3 和 sn-1-palmitoyl-2-myristoyl-3-(N-stearoyl-6-dehydroxy-6-amino-α-glucosyl)glycerol 4 通过简便有效的合成策略首次被合成。其关键步骤为：三氯亚胺酯糖基供体 10 与 (S)-isopropyleneglycerol 在乙醚溶液中发生糖苷化反应，立体选择性的生成3-O-(2,3,4-tri-O-benzyl-6-dehydroxy-6-benzyloxycarbonylamino-α-D- glucopyranoyl)-1,2-O-isopropylene-sn- glycerol 7。中间体 7 经过脱除丙酮叉、与不同的脂肪酸缩合、脱除保护基和选择性的在氨基上酰化，最终得到目标化合物 3 和 4。

Synthesis of Natural α ‐6‐Dehydroxy‐6‐aminoglucoglycerolipids

Two natural 6‐dehydroxy‐6‐aminoglucoglycerolipids were first synthesized in a convenient approach. The key step was the selective α‐glycosylation of 6‐dehydroxy‐2,3,4‐tri‐O‐benzyl‐6‐amino‐D‐glucopyranosyl trichloroacetimidate donor 10 with (S)‐isopropyleneglycerol using diethyl ether as glycosylation solvent to give 3‐O‐(2,3,4‐tri‐O‐benzyl‐6‐dehydroxy‐6‐benzyloxycarbonylamino‐α‐D‐glucopyranoyl)‐1,2‐O‐isopropylene‐sn‐glycerol 7 . Removal of acetonide group of 7 and acylation with various fatty acids, then deprotection of benzyl and Cbz groups and selective acylation of the amino group afforded the marine natural glycoglycerolopids of sn‐1,2‐dipalmitoyl‐3‐(N‐palmitoyl‐6‐dehydroxy‐6‐amino‐α‐glucosyl)glycerol 3 and sn‐1‐palmitoyl‐2‐myristoyl‐3‐(N‐stearoyl‐6‐dehydroxy‐6‐amino‐α‐glucosyl)glycerol 4 . The structures of the synthetic samples were identified by ¹H, ¹³C NMR, and HRESIMS.