methyl 2,3,4-tri-O-acetyl-7-bromo-6,7-dideoxy-α-D-manno-heptopyranoside | 540501-05-1

• 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-acetyl-7-bromo-6,7-dideoxy-α-D-manno-heptopyranoside
• CAS: 540501-05-1
• 化学式: C₁₄H₂₁BrO₈
• 分子量: 397.22
• InChiKey: MHPDSQKLZRAWTG-DGTMBMJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.94
• 重原子数：
  23.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  97.36
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  methyl 2,3,4-tri-O-acetyl-7-bromo-6,7-dideoxy-α-D-manno-heptopyranoside 在 2,4,6-三甲基吡啶 、 硫酸 、 氢溴酸 、 silver trifluoromethanesulfonate 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 40.25h， 生成 2,3,4-tri-O-acetyl-7-bromo-6,7-dideoxy-1,2-O-[8-(cholest-5-en-3β-yloxy)-3,6-dioxaoctan-1-yloxyethylidene]-β-D-manno-heptopyranose
  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-deoxy-6-C-formyl-α-D-mannopyranoside 在 palladium on activated charcoal 吡啶 、 sodium tetrahydroborate 、 氢气 、 lithium bromide 作用下， 以 乙醇 、 水 、 丁酮 为溶剂， 反应 23.08h， 生成 methyl 2,3,4-tri-O-acetyl-7-bromo-6,7-dideoxy-α-D-manno-heptopyranoside
  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