methyl 4,6-O-benzylidene-2,3-dideoxy-3-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyloxy)amino-α-D-ribo-hexopyranoside | 612050-34-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4,6-O-benzylidene-2,3-dideoxy-3-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyloxy)amino-α-D-ribo-hexopyranoside
• 英文别名: (2R,4aR,6S,8S,8aS)-6-methoxy-2-phenyl-N-[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-amine
• CAS: 612050-34-7
• 化学式: C₄₈H₅₃NO₁₀
• 分子量: 803.95
• InChiKey: CIMLBESSRLFCKS-BSIFIWMZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  59
• 可旋转键数：
  18
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl 4,6-O-benzylidene-2,3-dideoxy-3-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyloxy)amino-α-D-ribo-hexopyranoside 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以84%的产率得到methyl 2,3-dideoxy-3-(α-D-glucopyranosyloxy)amino-α-D-ribo-hexopyranoside
  参考文献：
  名称：

  Synthesis of a novel N–O-interglycosidic disaccharide

  摘要：

  The carbohydrate subunits carrying an N-O-interglycosidic bond play a very important role in the biological activity of the enediyne antibiotics. Condensation of O-(alpha- and beta-D-glucopyranosyl)hydroxylamine (5a and 5b) with the hex-3-ulopyranoside (6) furnished methyl 4,6-O-benzylidene-2,3-dideoxy-3-(2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranosyloxy)imino-alpha- and beta-D-erythro-hexopyranoside (7a and 7b). Stereoselective reduction of the C=N bond of 7a and 7b with sodium cyanoborohydride resulted in the formation of the required protected N-O-interglycosidic disaccharides (8a and 8b). Finally, catalytic hydrogenation of 8a afforded methyl 2,3-dideoxy-3-(alpha-D-glucopyranosyloxy)amino-alpha-D-ribo-hexopyranoside (9a). Under similar conditions the beta anomer 8b underwent decomposition. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00270-2
• 作为产物：
  描述：

  phthalimidyl 2,3,4,6-tetra-O-benzyl-D-glucopyranoside 在 盐酸 、 sodium cyanoborohydride 、 一水合肼 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 51.0h， 生成 methyl 4,6-O-benzylidene-2,3-dideoxy-3-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyloxy)amino-α-D-ribo-hexopyranoside
  参考文献：
  名称：

  Synthesis of a novel N–O-interglycosidic disaccharide

  摘要：

  The carbohydrate subunits carrying an N-O-interglycosidic bond play a very important role in the biological activity of the enediyne antibiotics. Condensation of O-(alpha- and beta-D-glucopyranosyl)hydroxylamine (5a and 5b) with the hex-3-ulopyranoside (6) furnished methyl 4,6-O-benzylidene-2,3-dideoxy-3-(2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranosyloxy)imino-alpha- and beta-D-erythro-hexopyranoside (7a and 7b). Stereoselective reduction of the C=N bond of 7a and 7b with sodium cyanoborohydride resulted in the formation of the required protected N-O-interglycosidic disaccharides (8a and 8b). Finally, catalytic hydrogenation of 8a afforded methyl 2,3-dideoxy-3-(alpha-D-glucopyranosyloxy)amino-alpha-D-ribo-hexopyranoside (9a). Under similar conditions the beta anomer 8b underwent decomposition. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(03)00270-2

文献信息

• Synthesis of a novel N–O-interglycosidic disaccharide
  作者：Miklós Hornyák、Ferenc Sztaricskai、István F. Pelyvás、Gyula Batta

  DOI：10.1016/s0008-6215(03)00270-2

  日期：2003.8

  The carbohydrate subunits carrying an N-O-interglycosidic bond play a very important role in the biological activity of the enediyne antibiotics. Condensation of O-(alpha- and beta-D-glucopyranosyl)hydroxylamine (5a and 5b) with the hex-3-ulopyranoside (6) furnished methyl 4,6-O-benzylidene-2,3-dideoxy-3-(2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranosyloxy)imino-alpha- and beta-D-erythro-hexopyranoside (7a and 7b). Stereoselective reduction of the C=N bond of 7a and 7b with sodium cyanoborohydride resulted in the formation of the required protected N-O-interglycosidic disaccharides (8a and 8b). Finally, catalytic hydrogenation of 8a afforded methyl 2,3-dideoxy-3-(alpha-D-glucopyranosyloxy)amino-alpha-D-ribo-hexopyranoside (9a). Under similar conditions the beta anomer 8b underwent decomposition. (C) 2003 Elsevier Ltd. All rights reserved.