保护的β-2-脱氧-2-氨基葡三糖的合成

Synthesis of Protected 2-Amino-2-deoxytriglucose

以茴香醛保护氨基方法得到的β-构型的四乙酰基氨基葡萄糖盐酸盐(1)为原料,采用三氯乙酰基(TCA)、三氯乙酰亚胺酯基(TCI)和乙硫基(SEt)保护体系,经五步反应以产率40.5%得到完全β-构型保护的β-(1→3)-2-脱氧-2-氨基葡二糖7,又经两步合成得到保护的β-(1→3)-2-脱氧-2-氨基葡二糖受体8,共八步合成了保护的β-(1→3)-2-脱氧-2-氨基葡三糖10,总产率为27%.以上化合物均为未知.同时,还得到了用以合成β-(1→4)-保护的氨基葡四糖的受体6.采用该保护体系可以高选择性地、较高产率地合成氨基寡糖.

By using trichloroacetyl, trichloroacetimidate group and ethylthio as the protection system and through five steps, protected β-（1→3）-2-amino-2-deoxydiglucose 7 was synthesized from β-tetra-O-acetyl-glucosylamine hydrochloride （1）. β-（1→3）-2-amino-2-deoxydiglucose acceptor 8 was also produced by two steps. Finally protected β-（1→3）-2-amino-2-deoxytriglucose 10 was obtained through eight steps with the tolal yield of 27%. These compounds are all new ones. Using this protection system, aminooligosaccharides can be selectively synthesized with high yield.