butyl 2,3,4,6-tetra-O-(trimethylsilyl)-α-D-mannopyranoside | 146399-94-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: butyl 2,3,4,6-tetra-O-(trimethylsilyl)-α-D-mannopyranoside
• CAS: 146399-94-2
• 化学式: C₂₂H₅₂O₆Si₄
• 分子量: 524.993
• InChiKey: ROFXRSZDKHHNAI-AANPDWTMSA-N

物化性质

• 沸点：
  445.0±45.0 °C(predicted)
• 密度：
  0.95±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.04
• 重原子数：
  32.0
• 可旋转键数：
  13.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.38
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  butyl 2,3,4,6-tetra-O-(trimethylsilyl)-α-D-mannopyranoside 在 N-乙基吗啉 、 水 、 potassium carbonate 、 三氯氧磷 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 butyl α-D-mannopyranoside 6-phosphate
  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：

  2,3,4,6-Tetra-O-benzoyl-α-D-mannopyranosyl bromide 在 吡啶 、 sodium methylate 、 silver trifluoromethanesulfonate 、 1,1,3,3-四甲基脲 作用下， 以 甲醇 为溶剂， 反应 4.0h， 生成 butyl 2,3,4,6-tetra-O-(trimethylsilyl)-α-D-mannopyranoside
  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.