methyl 2,3,4-tri-O-benzyl-6-deoxy-7-bromo-α-D-mannoheptopyranoside | 540501-02-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4-tri-O-benzyl-6-deoxy-7-bromo-α-D-mannoheptopyranoside
• 英文别名: (2R,3R,4S,5S,6S)-2-(2-bromoethyl)-6-methoxy-3,4,5-tris(phenylmethoxy)oxane
• CAS: 540501-02-8
• 化学式: C₂₉H₃₃BrO₅
• 分子量: 541.482
• InChiKey: QVOVJLCPDBMXAA-PNHLWVRCSA-N

物化性质

• 沸点：
  608.7±55.0 °C(predicted)
• 密度：
  1.30±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-benzyl-6-deoxy-7-bromo-α-D-mannoheptopyranoside 在 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 2-[(2R,3R,4S,5S,6S)-6-methoxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]ethylphosphonic acid
  参考文献：
  名称：

  A Flexible Route to Mannose 6-Phosphonate Functionalized Derivatives

  摘要：

  A new approach for the synthesis of a mannose 6-phosphonate isosteric analog of mannose 6-phosphate is reported. The mannosylphosphonate has been prepared in a multistep synthesis involving an homologation reaction of the methyl alpha-D-mannopyranoside followed by an Arbuzov reaction between a bromohomomannosyl derivative and the tris(trimethylsilyl)phosphite. This approach, avoiding the deprotection of dialkylphosphonate, allowed us to prepare the mannose 6-phosphonate in good yield. The described method was successfully extended to the preparation of a mannose 6-phosphonate linked to a cholesteryl moiety. This strategy affords a more general route for a wide range of functionalized mannose 6-phosphonate derivatives.

  DOI：

  10.1080/10426500214297
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-benzyl-6-O-(trifluoromethanesulfonyl)-α-D-mannopyranoside 在 六甲基磷酰三胺 、 sodium tetrahydroborate 、 正丁基锂 、 ammonium cerium(IV) nitrate 、 N,N-二异丙基乙胺 、 lithium bromide 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 、 乙腈 、 丁酮 为溶剂， 反应 1.83h， 生成 methyl 2,3,4-tri-O-benzyl-6-deoxy-7-bromo-α-D-mannoheptopyranoside
  参考文献：
  名称：

  A Flexible Route to Mannose 6-Phosphonate Functionalized Derivatives

  摘要：

  A new approach for the synthesis of a mannose 6-phosphonate isosteric analog of mannose 6-phosphate is reported. The mannosylphosphonate has been prepared in a multistep synthesis involving an homologation reaction of the methyl alpha-D-mannopyranoside followed by an Arbuzov reaction between a bromohomomannosyl derivative and the tris(trimethylsilyl)phosphite. This approach, avoiding the deprotection of dialkylphosphonate, allowed us to prepare the mannose 6-phosphonate in good yield. The described method was successfully extended to the preparation of a mannose 6-phosphonate linked to a cholesteryl moiety. This strategy affords a more general route for a wide range of functionalized mannose 6-phosphonate derivatives.

  DOI：

  10.1080/10426500214297