[(3aR,5R,6R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] (1R)-1-phenylethanesulfonate | 424839-30-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: [(3aR,5R,6R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] (1R)-1-phenylethanesulfonate
• CAS: 424839-30-5
• 化学式: C₂₀H₂₈O₈S
• 分子量: 428.504
• InChiKey: NRHNYXOQWZRJMP-NOCPITAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  97.9
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  [(3aR,5R,6R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] (1R)-1-phenylethanesulfonate 在 palladium diacetate 作用下， 以 乙醚 、 乙醇 、 水 为溶剂， 反应 96.0h， 生成 (R)-methyl 1-phenylethanesulfonate
  参考文献：
  名称：

  Efficient asymmetric synthesis of α-alkylated benzylic methyl sulfonates

  摘要：

  The first highly efficient auxiliary-controlled synthesis of various alpha-substituted sulfortic acid derivatives is described. Alkyl or aryl halides were reacted with lithiated benzylic sulfortic esters bearing 1,2:5,6-di-O-isopropylidene-alpha-D-allofuranose as a removable enantiopure alcohol auxiliary to give the alkylated products in excellent diastereomeric excesses. The racemization-free cleavage conditions provided highly enantioenriched sulfonic acid derivatives (ee >= 98%). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.046
• 作为产物：
  描述：

  苄磺酰氯 在 正丁基锂 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 25.0h， 生成 [(3aR,5R,6R,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] (1R)-1-phenylethanesulfonate
  参考文献：
  名称：

  Efficient asymmetric synthesis of α-alkylated benzylic methyl sulfonates

  摘要：

  The first highly efficient auxiliary-controlled synthesis of various alpha-substituted sulfortic acid derivatives is described. Alkyl or aryl halides were reacted with lithiated benzylic sulfortic esters bearing 1,2:5,6-di-O-isopropylidene-alpha-D-allofuranose as a removable enantiopure alcohol auxiliary to give the alkylated products in excellent diastereomeric excesses. The racemization-free cleavage conditions provided highly enantioenriched sulfonic acid derivatives (ee >= 98%). (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.01.046

文献信息

• The First Highly Efficient Asymmetric Synthesis of α-Substituted Methyl Sulfonates
  作者：Dieter Enders、Nicola Vignola、Otto M. Berner、Jan W. Bats

  DOI：10.1002/1521-3773(20020104)41:1<109::aid-anie109>3.0.co;2-f

  日期：2002.1.4