[(3aR,5R,6S,6aR)-5-[(1R)-1-hydroxy-2-[(2-methylpropan-2-yl)oxy]ethyl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] 4-methylbenzenesulfonate | 145125-27-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: [(3aR,5R,6S,6aR)-5-[(1R)-1-hydroxy-2-[(2-methylpropan-2-yl)oxy]ethyl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] 4-methylbenzenesulfonate
• CAS: 145125-27-5
• 化学式: C₂₀H₃₀O₈S
• 分子量: 430.519
• InChiKey: LPOPUGGJYVAXDO-UYTYNIKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [(3aR,5R,6S,6aR)-5-[(1R)-1-hydroxy-2-[(2-methylpropan-2-yl)oxy]ethyl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] 4-methylbenzenesulfonate 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 生成 Toluene-4-sulfonic acid (3aR,5S,6R,6aR)-5-(2-tert-butoxy-acetyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester
  参考文献：
  名称：

  An Efficient Procedure for the Regioselective Monoprotection of 1,2-Diols

  摘要：

  Nucleophilic ring opening of isopropylidene ketals by trimethylaluminum is described. This reagent offers a new method for selective monoprotection of 1,2-diols. The regioselectivity of this reaction was studied with simple diols and with carbohydrates.

  DOI：

  10.1016/s0040-4020(01)86582-0
• 作为产物：
  描述：

  三甲基铝 、 1,2:5,6-di-O-isopropylidene-3-O-tosyl-α-D-glucofuranoside 以 二氯甲烷 为溶剂， 以98%的产率得到[(3aR,5R,6S,6aR)-5-[(1R)-1-hydroxy-2-[(2-methylpropan-2-yl)oxy]ethyl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] 4-methylbenzenesulfonate
  参考文献：
  名称：

  An Efficient Procedure for the Regioselective Monoprotection of 1,2-Diols

  摘要：

  Nucleophilic ring opening of isopropylidene ketals by trimethylaluminum is described. This reagent offers a new method for selective monoprotection of 1,2-diols. The regioselectivity of this reaction was studied with simple diols and with carbohydrates.

  DOI：

  10.1016/s0040-4020(01)86582-0