支链糖的合成：一条从共同前体立体选择性合成西伯利亚胺、甘露糖胺和维内洛糖的路线。
Synthesis of branched-chain sugars: a stereoselective route to sibirosamine, kansosamine, and vinelose from a common precursor.
作者信息
Giuliano R M, Kasperowicz S
机构信息
Department of Chemistry, Villanova University, PA 19085.
出版信息
Carbohydr Res. 1988 Dec 1;183(2):277-85. doi: 10.1016/0008-6215(88)84080-1.
Methyl 4,6-dideoxy-3-C-methyl-4-(N-methyl-N-phenylsulfonylamino)-alpha-L- mannopyranoside and methyl 4-amino-4,6-dideoxy-3-C-methyl-alpha-L-mannopyranoside, derivatives of the branched-chain amino sugars sibirosamine and kansosamine, respectively, were synthesized by nucleophilic ring-opening of methyl 3,4-anhydro-6-deoxy-3-C-methyl-alpha-L-talopyranoside. Catalytic reduction of methyl 6-deoxy-2,3-O-isopropylidene-3-C-methyl-alpha-L-lyxo-hexopyrano sid-4-ulose gave the axial alcohol methyl 6-deoxy-2,3-O-isopropylidene-3-C-methyl-alpha-L-talopyranoside, a known precursor to vinelose.
4,6-二脱氧-3-C-甲基-4-(N-甲基-N-苯基磺酰氨基)-α-L-甘露吡喃糖苷甲酯和4-氨基-4,6-二脱氧-3-C-甲基-α-L-甘露吡喃糖苷甲酯，分别是支链氨基糖西伯利亚胺和甘露糖胺的衍生物，由3,4-脱水-6-脱氧-3-C-甲基-α-L-塔罗吡喃糖苷甲酯的亲核开环反应合成。6-脱氧-2,3-O-异亚丙基-3-C-甲基-α-L-来苏己吡喃糖-4-酮甲酯的催化还原得到轴向醇6-脱氧-2,3-O-异亚丙基-3-C-甲基-α-L-塔罗吡喃糖苷甲酯，它是维内洛糖的已知前体。
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