新型海参硫酸软骨素葡萄糖受体及葡萄糖醛酸受体的高效合成

以D-葡萄糖为起始原料，经9步反应合成了2-O-苄基-3-O-烯丙基-1-O-对甲氧基苯基α-D-葡萄糖(9)；将9的6-位伯羟基经叔丁基二苯基硅烷基(TBDPS)保护，首次合成了正交保护的新型葡萄糖受体2-O-苄基-3-O-烯丙基6-O-叔丁基二苯基硅烷基1-O-对甲氧基苯基α-D-葡萄糖(Ⅱ)，总收率28.2%；将9的6-位伯羟基氧化糖醛酸化后，再经甲酯化，以25.0%的总收率首次合成了新型葡萄糖醛酸受体2-O-苄基-3-O-烯丙基-1-O-对甲氧基苯基α-D-葡萄糖醛酸甲酯(Ⅲ),化合物结构经¹H NMR，¹³C NMR， IR和HR-MS(ESI)表征。

Efficient Synthesis of Novel Glucose and Glucuronic Acid Acceptors for Sea Cucumber Chondroitin Sulfate Preparation

p-Methoxyphenyl 2-O-benzyl-3-O-allyl-α-D-glucopyranoside ( 9 ) was synthesized from D-glucose by nine step reactions. The primary hydroxyl of 9 was protected by tert-butyldiphenysilyl( TB-DPS) to afford the novel orthogonal protected glucose acceptor p-methoxyphenyl 2-O-benzyl-3-O-allyl-6-O-tert-butyldiphenysilyl-α-D-glucopyranoside(Ⅱ) for the first time, in total yield of 28. 2%. Oxida-tion of the primary hydroxyl of 9, followed by esterification with iodine methane, provided the new glucu-ronic acid acceptor methyl ( p-methoxyphenyl 2-O-benzyl-3-O-allyl-α-D-glucopyranoside ) uronate (Ⅲ) , in total yield of 25. 0%. The structures were characterized by 1 H NMR, 13 C NMR and HR-MS( ESI) .