(3aS,4S,6R,6aS)-6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-4-phenylmethoxy-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole | 272780-73-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aS,4S,6R,6aS)-6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-4-phenylmethoxy-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole
• CAS: 272780-73-1
• 化学式: C₁₉H₂₆O₆
• 分子量: 350.412
• InChiKey: FDOXFJBHCHWEOL-QEOTZNIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (3aS,4S,6R,6aS)-6-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-4-phenylmethoxy-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole 在 甲醇 作用下， 反应 0.5h， 以92%的产率得到benzyl 2,3-O-isopropylidene-β-L-gulofuranoside
  参考文献：
  名称：

  Ultrasound-Assisted Selective Deprotection of Terminal Acetonides Catalyzed by Silica-Supported Boron Trifluoride

  摘要：

  An efficient and convenient method for the selective cleavage of terminal acetonides is described. Treatment of terminal acetonides in the presence of a wide range of functional groups with silica-supported boron trifluoride as a catalyst furnished the corresponding diols in 8295% yield under ultrasound irradiation conditions. The acid-labile p-methoxybenzyl group as a protecting group remained intact under the conditions employed to the present deprotection condition.

  DOI：

  10.1080/07328303.2012.762980