A Convenient Synthesis of Furanose-Free D-Fucose Per-O-Acetates and a Precursor for Anthrose
A Convenient Synthesis of Furanose-Free D-Fucose Per-O-Acetates and a Precursor for Anthrose
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无呋喃糖 D-岩藻糖过氧乙酸酯和炭疽病前体的便捷合成
DOI：
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发表时间：
2008
期刊：
影响因子：
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通讯作者：
P. Kováč
中科院分区：
文献类型：
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作者：
Shu;P. Kováč
甲基3，4-O-异亚丙基-α-或β-D-吡喃半乳糖苷在三苯基膦存在下与三碘咪唑发生碘化反应，相应的6-脱氧-6-碘代衍生物5或6分别转化为不含呋喃糖的1，2，3，4-四-O-乙酰基-α，β-D-吡喃岩藻糖。以5或6为起始原料，经7步反应合成了炭疽芽孢杆菌外孢主要糖蛋白四糖的关键中间体1-O-乙酰基-4-叠氮基-2-O-苯甲酰基-3-O-苄基-4，6-双脱氧-α，β-D-吡喃葡萄糖。后者很容易转化为相应的1-O-三氯乙酰亚胺酯。（© Wiley-VCH Verlag GmbH & Co. KGaA，69451魏因海姆，德国，2008）
Methyl 3,4-O-isopropylidene-α- or β-D-galactopyranoside was iodinated with triiodoimidazole in the presence of triphenylphosphane and the corresponding 6-deoxy-6-iodo derivatives 5 or 6, respectively, were converted to furanose-free 1,2,3,4-tetra-O-acetyl-α,β-D-fucopyranose. A key intermediate for chemical synthesis of anthrose, a constituent of the tetrasaccharide of major glycoprotein of Bacillus anthracis exosporium, 1-O-acetyl-4-azido-2-O-benzoyl-3-O-benzyl-4,6-dideoxy-α,β-D-glucopyranose, was synthesized from 5 or 6 in 7 steps. The latter was readily converted into the corresponding 1-O-trichloroacetimidate.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
影响因子：
3.1
作者：
Saksena,Rina;Adamo,Roberto;Kovac,Pavol
通讯作者：
Kovac,Pavol