4-methoxycarbonyl-2-nitrobenzyl 3,4,6-tri-O-benzyl-2-O-tert-butyldimethylsilyl-α-D-mannopyranoside | 865280-81-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-methoxycarbonyl-2-nitrobenzyl 3,4,6-tri-O-benzyl-2-O-tert-butyldimethylsilyl-α-D-mannopyranoside
• 英文别名: methyl 4-[[(2S,3S,4S,5R,6R)-3-[tert-butyl(dimethyl)silyl]oxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxymethyl]-3-nitrobenzoate
• CAS: 865280-81-5
• 化学式: C₄₂H₅₁NO₁₀Si
• 分子量: 757.953
• InChiKey: VDJRZDYKWBBFLR-BWLXSFHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.4
• 重原子数：
  54
• 可旋转键数：
  18
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  128
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4-methoxycarbonyl-2-nitrobenzyl 3,4,6-tri-O-benzyl-2-O-tert-butyldimethylsilyl-α-D-mannopyranoside 在 氢氧化钾 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 生成 4-[(2S,3S,4S,5R,6R)-4,5-Bis-benzyloxy-3-((3aS,4R,6R,7R,7aS)-7-benzyloxy-6-benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yloxy)-6-benzyloxymethyl-tetrahydro-pyran-2-yloxymethyl]-3-nitro-benzoic acid
  参考文献：
  名称：

  Oligosaccharide synthesis on a soluble, hyperbranched polymer support via thioglycoside activation

  摘要：

  The synthesis of linear and branched di-, tri- and tetramannosides on a commercially available hyperbranched polyester as a soluble, high loading support is described. Gil/cosylation products were isolated in 26-63% yield as mixtures of anomers after total hydrolytic degradation of the polymer. All polymer-bound intermediates were purified through simple extraction or precipitation. Solution phase NMR and MALDI-TOF were used to monitor the progress of the reaction directly on the hyperbranched polymer support. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.06.101
• 作为产物：
  描述：

  4-methoxycarbonyl-2-nitrobenzyl 2-O-acetyl-3,4,6-tri-O-benzyl-D-mannopyranoside 在 2,6-二甲基吡啶 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 6.75h， 生成 4-methoxycarbonyl-2-nitrobenzyl 3,4,6-tri-O-benzyl-2-O-tert-butyldimethylsilyl-α-D-mannopyranoside
  参考文献：
  名称：

  Oligosaccharide synthesis on a soluble, hyperbranched polymer support via thioglycoside activation

  摘要：

  The synthesis of linear and branched di-, tri- and tetramannosides on a commercially available hyperbranched polyester as a soluble, high loading support is described. Gil/cosylation products were isolated in 26-63% yield as mixtures of anomers after total hydrolytic degradation of the polymer. All polymer-bound intermediates were purified through simple extraction or precipitation. Solution phase NMR and MALDI-TOF were used to monitor the progress of the reaction directly on the hyperbranched polymer support. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.06.101