6-O-dichlorophosphinyl-1,2,3,4-tetra-O-(trimethylsilyl)-α-D-mannopyranose | 146399-92-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-dichlorophosphinyl-1,2,3,4-tetra-O-(trimethylsilyl)-α-D-mannopyranose
• 英文别名: [(2R,3R,4S,5S,6R)-2-(dichlorophosphoryloxymethyl)-3,5,6-tris(trimethylsilyloxy)oxan-4-yl]oxy-trimethylsilane
• CAS: 146399-92-0
• 化学式: C₁₈H₄₃Cl₂O₇PSi₄
• 分子量: 585.757
• InChiKey: COVAFGODPSVEBC-DFBDCSAJSA-N

物化性质

• 沸点：
  480.6±45.0 °C(Predicted)
• 密度：
  1.09±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.83
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-O-dichlorophosphinyl-1,2,3,4-tetra-O-(trimethylsilyl)-α-D-mannopyranose 在 水 作用下， 生成 α-D-mannopyranose-6-phosphate 、 甘露糖磷酸酯
  参考文献：
  名称：

  Large-scale synthesis of d-mannose 6-phosphate and other hexose 6-phosphates

  摘要：

  The syntheses of D-mannose 6-phosphate (4), several D-mannopyranoside 6-phosphates, and methyl alpha-D-glucopyranoside 6-phosphate are described. Phosphorylation of methyl 2,3,4-tri-O-(trimethylsilyl)-alpha-D-mannopyranoside (2) with phosphorus oxychloride followed by careful hydrolysis gave methyl alpha-D-mannopyranoside 6-phosphate (10, 81%). Direct phosphorylation of 1,2,3,4,6-penta-O-(trimethylsiyl)-alpha-D-mannopyranoside with phosphorus oxychloride followed by hydrolysis gave 4 (50% yield based on D-mannose). The first method was further used in the synthesis of methyl, butyl, and hexadecyl alpha-D-mannopyranoside 6-phosphate disodium salts, and in the synthesis of methyl alpha-D-glucopyranoside 6-phosphate disodium salt.Compound 2 was obtained in 67% yield, from methyl 2,3,4,6-tetra-O-(trimethylsilyl)-alpha-D-mannopyranoside, by selective hydrolysis with a saturated solution of potassium carbonate in methanol.Butyl and hexadecyl alpha-D-mannopyranosides were prepared by glycosidation of the respective alcohols with tetra-O-benzoyl-alpha-D-mannopyranosyl bromide in silver triflate-promoted reactions.

  DOI：

  10.1016/0008-6215(92)80082-c
• 作为产物：
  描述：

  D-甘露糖 在 吡啶 、 三氯氧磷 作用下， 以 甲苯 为溶剂， 反应 1.0h， 生成 6-O-dichlorophosphinyl-1,2,3,4-tetra-O-(trimethylsilyl)-α-D-mannopyranose
  参考文献：
  名称：

  Large-scale synthesis of d-mannose 6-phosphate and other hexose 6-phosphates

  摘要：

  The syntheses of D-mannose 6-phosphate (4), several D-mannopyranoside 6-phosphates, and methyl alpha-D-glucopyranoside 6-phosphate are described. Phosphorylation of methyl 2,3,4-tri-O-(trimethylsilyl)-alpha-D-mannopyranoside (2) with phosphorus oxychloride followed by careful hydrolysis gave methyl alpha-D-mannopyranoside 6-phosphate (10, 81%). Direct phosphorylation of 1,2,3,4,6-penta-O-(trimethylsiyl)-alpha-D-mannopyranoside with phosphorus oxychloride followed by hydrolysis gave 4 (50% yield based on D-mannose). The first method was further used in the synthesis of methyl, butyl, and hexadecyl alpha-D-mannopyranoside 6-phosphate disodium salts, and in the synthesis of methyl alpha-D-glucopyranoside 6-phosphate disodium salt.Compound 2 was obtained in 67% yield, from methyl 2,3,4,6-tetra-O-(trimethylsilyl)-alpha-D-mannopyranoside, by selective hydrolysis with a saturated solution of potassium carbonate in methanol.Butyl and hexadecyl alpha-D-mannopyranosides were prepared by glycosidation of the respective alcohols with tetra-O-benzoyl-alpha-D-mannopyranosyl bromide in silver triflate-promoted reactions.

  DOI：

  10.1016/0008-6215(92)80082-c

文献信息

• Large-scale synthesis of d-mannose 6-phosphate and other hexose 6-phosphates
  作者：Morten Meldal、Mette Knak Christensen、Klaus Bock

  DOI：10.1016/0008-6215(92)80082-c

  日期：1992.11

  The syntheses of D-mannose 6-phosphate (4), several D-mannopyranoside 6-phosphates, and methyl alpha-D-glucopyranoside 6-phosphate are described. Phosphorylation of methyl 2,3,4-tri-O-(trimethylsilyl)-alpha-D-mannopyranoside (2) with phosphorus oxychloride followed by careful hydrolysis gave methyl alpha-D-mannopyranoside 6-phosphate (10, 81%). Direct phosphorylation of 1,2,3,4,6-penta-O-(trimethylsiyl)-alpha-D-mannopyranoside with phosphorus oxychloride followed by hydrolysis gave 4 (50% yield based on D-mannose). The first method was further used in the synthesis of methyl, butyl, and hexadecyl alpha-D-mannopyranoside 6-phosphate disodium salts, and in the synthesis of methyl alpha-D-glucopyranoside 6-phosphate disodium salt.Compound 2 was obtained in 67% yield, from methyl 2,3,4,6-tetra-O-(trimethylsilyl)-alpha-D-mannopyranoside, by selective hydrolysis with a saturated solution of potassium carbonate in methanol.Butyl and hexadecyl alpha-D-mannopyranosides were prepared by glycosidation of the respective alcohols with tetra-O-benzoyl-alpha-D-mannopyranosyl bromide in silver triflate-promoted reactions.