O-（N-乙酰基-α-D-神经氨酰基）-（2→3）-O-β-D-吡喃半乳糖基-（1→3）-O- [（N-乙酰基-α-D-神经氨酰基）-（2→6）]-O-（2-乙酰氨基-2-脱氧-α-D-吡喃半乳糖基）-（1→3）-L-丝氨酸的全保护衍生物的合成
Synthesis of a fully protected derivative of O-(N-acetyl-alpha-D-neuraminyl)-(2----3)-O-beta-D-galactopyranosyl-(1- ---3)-O- [(N-acetyl-alpha-D-neuraminyl)-(2----6)]-O-(2-acetamido-2-deoxy-alpha- D-galactopyranosyl)-(1----3)-L-serine.
作者信息
Iijima H, Ogawa T
机构信息
RIKEN Institute of Physical and Chemical Research, Saitama, Japan.
出版信息
Carbohydr Res. 1989 Feb 15;186(1):107-18. doi: 10.1016/0008-6215(89)84009-1.
N-(Benzyloxycarbonyl)-O-[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-alpha-D-galact o-2- nonulopyranosyl)onate]-(2----3)-O-(2,4,6-tri-O-acetyl-beta-D - galactopyranosyl)-(1----3)-O-[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-alpha-D-galact o-2- nonulopyranosyl)onate-(2----6)]-O-(2-acetamido-4-O-acetyl-2- deoxy-alpha-D- galactopyranosyl)-(1----3)-L-serine benzyl ester was synthesized by using O-[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5- di-deoxy-D-glycero-alpha-D-galacto-2-nonulopyranosyl)onate]- (2----3)-O-(2,4,6- tri-O-acetyl-beta-D-galactopyranosyl)-(1----3)-O-[methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-alpha-D-galact o-2- nonulopyranosyl)onate-(2----6)]-4-O-acetyl-2-azido-2-deoxy-a lpha- and -beta-D-galactopyranosyl trichloroacetimidate as a key glycotetraosyl donor which, upon reaction with N-(benzyloxycarbonyl)-L-serine benzyl ester, afforded a 44% yield of a mixture of the alpha- and beta-glycosides in the ratio of 2:5.
通过使用O-[甲基(5-乙酰氨基-4,7,8,9-四-O-乙酰基-3,5-二脱氧-D-甘油-α-D-半乳糖-2-壬糖醛酸酯)]-(2→3)-O-(2,4,6-三-O-乙酰基-β-D-吡喃半乳糖基)-(1→3)-O-[甲基(5-乙酰氨基-4,7,8,9-四-O-乙酰基-3,5-二脱氧-D-甘油-α-D-半乳糖-2-壬糖醛酸酯)-(2→6)]-4-O-乙酰基-2-叠氮基-2-脱氧-α-和-β-D-吡喃半乳糖基三氯乙酰亚胺酯作为关键的糖四糖供体，合成了N-(苄氧羰基)-O-[甲基(5-乙酰氨基-4,7,8,9-四-O-乙酰基-3,5-二脱氧-D-甘油-α-D-半乳糖-2-壬糖醛酸酯)]-(2→3)-O-(2,4,6-三-O-乙酰基-β-D-吡喃半乳糖基)-(1→3)-O-[甲基(5-乙酰氨基-4,7,8,9-四-O-乙酰基-3,5-二脱氧-D-甘油-α-D-半乳糖-2-壬糖醛酸酯)-(2→6)]-O-(2-乙酰氨基-4-O-乙酰基-2-脱氧-α-D-吡喃半乳糖基)-(1→3)-L-丝氨酸苄酯。该供体与N-(苄氧羰基)-L-丝氨酸苄酯反应，得到了产率为44%的α-和β-糖苷混合物，其比例为2:5。
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