1,6-di-O-acetyl-2-azido-3-O-benzyl-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl)-2-deoxy-D-glucopyranose | 848850-47-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1,6-di-O-acetyl-2-azido-3-O-benzyl-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl)-2-deoxy-D-glucopyranose
• 英文别名: [(2R,3S,4R,5R)-6-acetyloxy-5-azido-3-[(2S,3R,4R,5S,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-3-(2,2,2-trichloroethoxycarbonylamino)oxan-2-yl]oxy-4-phenylmethoxyoxan-2-yl]methyl acetate
• CAS: 848850-47-5
• 化学式: C₃₂H₃₉Cl₃N₄O₁₆
• 分子量: 842.038
• InChiKey: VSQQKYTUGAOLMU-LFFHHHHESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  55
• 可旋转键数：
  21
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  221
• 氢给体数：
  1
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  1,6-di-O-acetyl-2-azido-3-O-benzyl-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl)-2-deoxy-D-glucopyranose 在 2,4,6-三甲基吡啶 、 氢溴酸 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 反应 19.58h， 生成 [(2R,3S,4R,5R,6S)-5-azido-3-[(2S,3R,4R,5S,6R)-4,5-diacetyloxy-6-(acetyloxymethyl)-3-(2,2,2-trichloroethoxycarbonylamino)oxan-2-yl]oxy-6-(4-methyl-2-oxochromen-7-yl)oxy-4-phenylmethoxyoxan-2-yl]methyl acetate
  参考文献：
  名称：

  α:β Selectivity in the synthesis of 3-substituted, 4-methyl umbelliferone glycosides of N-acetyl glucosamine and chitobiose

  摘要：

  The influence of phenolic acceptor nucleophilicity; for example, 3-substituted, 4-methylumbelliferones, and glycosyl donor electrophilicity; for example, 3- and 4-substituted N-acetylglucosamines, on glycosylation stereochemistry has been evaluated. In a systematic comparison, the stereochemical outcome as well as the reaction yield appeared to be influenced by the 3- and 4-substituents of the donor as well as the 3-substituent of the aryl acceptor. In the context of synthesizing a fluorogenic substrate for oligosaccharyltransferase, an alpha-glycoside was desired. Although most acceptor-donor pairs led to predominantly or exclusively the beta-glycoside, reaction of the most activated (3,4-di-O-benzyl) donor and the least nucleophilic acceptor (3-Br), resulted in a 1:1 ratio of alpha,beta arylglycosides. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.053
• 作为产物：
  描述：

  1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose 在 silver trifluoromethanesulfonate 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 生成 1,6-di-O-acetyl-2-azido-3-O-benzyl-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl)-2-deoxy-D-glucopyranose
  参考文献：
  名称：

  α:β Selectivity in the synthesis of 3-substituted, 4-methyl umbelliferone glycosides of N-acetyl glucosamine and chitobiose

  摘要：

  The influence of phenolic acceptor nucleophilicity; for example, 3-substituted, 4-methylumbelliferones, and glycosyl donor electrophilicity; for example, 3- and 4-substituted N-acetylglucosamines, on glycosylation stereochemistry has been evaluated. In a systematic comparison, the stereochemical outcome as well as the reaction yield appeared to be influenced by the 3- and 4-substituents of the donor as well as the 3-substituent of the aryl acceptor. In the context of synthesizing a fluorogenic substrate for oligosaccharyltransferase, an alpha-glycoside was desired. Although most acceptor-donor pairs led to predominantly or exclusively the beta-glycoside, reaction of the most activated (3,4-di-O-benzyl) donor and the least nucleophilic acceptor (3-Br), resulted in a 1:1 ratio of alpha,beta arylglycosides. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.053