Biosynthetic studies on the α-glucosidase inhibitor acarbose:: the chemical synthesis of dTDP-4-amino-4,6-dideoxy-α-D-glucose
Biosynthetic studies on the α-glucosidase inhibitor acarbose:: the chemical synthesis of dTDP-4-amino-4,6-dideoxy-α-D-glucose
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DOI：
10.1016/s0008-6215(01)00323-8
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发表时间：
2002-02-18
影响因子：
3.1
通讯作者：
Floss, HG
中科院分区：
文献类型：
--
作者：
Bowers, SG;Mahmud, T;Floss, HG
为了研究假四糖阿卡波糖的生物合成，从半乳糖经16步制备dTDP-4-氨基-4，6-二脱氧-α-D-葡萄糖（3）。在初始保护基团操作之后，通过甲苯磺酸酯的氢化物置换使半乳糖的6位脱氧。类似地，在与叠氮化钠反应时，4位的甲苯磺酰基被置换。通过糖基三氯乙酰亚氨酸酯与磷酸二苄酯的反应完成所得糖苷向糖基磷酸的转化。随后除去苄基保护基并通过氢化还原叠氮化物并与活化的核苷磷酸偶联，得到dTDP-4-氨基-4，6-二脱氧-α-D-葡萄糖。(C)2002爱思唯尔科技有限公司。保留所有权利。
To study the biosynthesis of the pseudotetrasaccharide acarbose, dTDP-4-amino-4,6-dideoxy-alpha-D-glucose (3) was prepared from galactose in 16 steps. After initial protecting-group manipulations, the 6-position of galactose was deoxygenated by hydride displacement of a tosylate. Similarly a tosyl group at the 4-position was displaced upon reaction with sodium azide. Conversion of the resulting glycoside to a glycosyl phosphate was accomplished by reaction of a glycosyl trichloroacetimidate with dibenzyl phosphate. Subsequent removal of the benzyl protecting groups and reduction of the azide by hydrogenation and coupling with an activated nucleoside phosphate gave dTDP-4-amino-4,6-dideoxy-alpha-D-glucose. (C) 2002 Elsevier Science Ltd. All rights reserved.