2,4-dinitro-6-(methoxycarbonyl)phenyl 3,4,6-tri-O-benzoyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside | 853014-85-4

• 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: 2,4-dinitro-6-(methoxycarbonyl)phenyl 3,4,6-tri-O-benzoyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside
• 英文别名: methyl 2-[(2R,3R,4R,5S,6R)-4,5-dibenzoyloxy-6-(benzoyloxymethyl)-3-(2,2,2-trichloroethoxycarbonylamino)oxan-2-yl]oxy-3,5-dinitrobenzoate
• CAS: 853014-85-4
• 化学式: C₃₈H₃₀Cl₃N₃O₁₆
• 分子量: 891.026
• InChiKey: PPSUFFRCDJGIJY-WETVODNCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  60
• 可旋转键数：
  17
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  254
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  2,4-dinitro-6-(methoxycarbonyl)phenyl 3,4,6-tri-O-benzoyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside 、 N-((4aR,6S,7R,8R,8aS)-8-Hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-acetamide 在 lithium perchlorate 作用下， 以 硝基甲烷 为溶剂， 反应 0.25h， 以38%的产率得到methyl 3,4,6-tri-O-benzoyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl-(1->3)-2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  Glucosamine derived DISAL donors for stereoselective glycosylations under neutral conditions

  摘要：

  DISAL (methyl 3,5-dinitrosa/icylate) D-glcosyl, D-galactosyl, D-mannosyl, and L-quinovosyl donors have previously provided the efficient glycosylation of a range of substrates under either strictly neutral, mildly basic, or very mildly Lewis acidic (LiClO4) conditions. Herein we report the synthesis of new glucosamine DISAL donors, carrying N-TCP, -Troc, or -TFAc protecting groups, and their use in beta-(1,2-trans) selective glycosylations, primarily in NMP in the absence of any added Lewis acids, or in CH3NO2 with LiClO4. Finally, precise microwave heating proved effective in promoting the difficult glycosylation of the 3-OH of a glucosamine derivative. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.02.029
• 作为产物：
  描述：

  3,4,6-tri-O-benzoyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α,β-D-glucopyranose 、 methyl 2-fluoro-3,5-dinitrobenzoic ester 在 4-二甲氨基吡啶 、 lithium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以95%的产率得到2,4-dinitro-6-(methoxycarbonyl)phenyl 3,4,6-tri-O-benzoyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside
  参考文献：
  名称：

  Glucosamine derived DISAL donors for stereoselective glycosylations under neutral conditions

  摘要：

  DISAL (methyl 3,5-dinitrosa/icylate) D-glcosyl, D-galactosyl, D-mannosyl, and L-quinovosyl donors have previously provided the efficient glycosylation of a range of substrates under either strictly neutral, mildly basic, or very mildly Lewis acidic (LiClO4) conditions. Herein we report the synthesis of new glucosamine DISAL donors, carrying N-TCP, -Troc, or -TFAc protecting groups, and their use in beta-(1,2-trans) selective glycosylations, primarily in NMP in the absence of any added Lewis acids, or in CH3NO2 with LiClO4. Finally, precise microwave heating proved effective in promoting the difficult glycosylation of the 3-OH of a glucosamine derivative. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.02.029