methyl 2,3,4,6-tetra-O-tert-butyldimethylsilyl-β-D-glucopyranoside | 116144-15-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,4,6-tetra-O-tert-butyldimethylsilyl-β-D-glucopyranoside
• CAS: 116144-15-1
• 化学式: C₃₁H₇₀O₆Si₄
• 分子量: 651.235
• InChiKey: CLDPSINVZRPNOV-IURCNINISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.55
• 重原子数：
  41.0
• 可旋转键数：
  10.0
• 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

• 作为产物：
  描述：

  叔丁基二甲基氯硅烷 、 甲基 Β-D-吡喃葡萄糖苷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以38%的产率得到methyl 2,3,4,6-tetra-O-tert-butyldimethylsilyl-β-D-glucopyranoside
  参考文献：
  名称：

  Studies of the selective silylation of methyl α- and β-d-aldohexopyranosides: stability of the partially protected derivatives in polar solvents

  摘要：

  Treatment of methyl .alpha.- (1) and .beta.-D-glucopyranosides, methyl .alpha.- (3) and .beta.-D-galactopyranosides, and methyl .alpha.-D-mannopyranoside (5) with 2, 3, or 4 mol. equiv. of tert-butyldimethylsilyl (TBDMS) chloride under two conditions afforded mixtures of TBDMS ethers which were identified. The following compounds were isolated in synthetically useful yields, the 2,6-di-TBDMS ether of 1 (70%), the 2,6-di- and 2,3,6-tri-TBDMS ethers of 3 (84% and 57%, respectively), and the 2,6-di- and 3,6-di-TBDMS ethers of 5 (50% and 80%, respectively). In dipolar solvents, no migration of the TBDMS groups was detected between partially silylated hydroxyl groups, but the addition of a base (triethylamine or imidazole) caused migration to vicinal cis positions.

  DOI：

  10.1016/0008-6215(87)85005-x