[(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)-2-naphthalen-2-yl-1-phenylethanesulfonate | 851518-55-3

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 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)-2-naphthalen-2-yl-1-phenylethanesulfonate
• CAS: 851518-55-3
• 化学式: C₃₀H₃₄O₈S
• 分子量: 554.661
• InChiKey: ZRXJDBUBNHFLFA-BXZOIBFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.87
• 重原子数：
  39.0
• 可旋转键数：
  7.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  89.52
• 氢给体数：
  0.0
• 氢受体数：
  8.0

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)-2-naphthalen-2-yl-1-phenylethanesulfonate 在 palladium diacetate 作用下， 以 乙醇 、 水 为溶剂， 反应 96.0h， 生成
  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：

  1,2:5,6-二异亚丙基-alpha-D-异呋喃糖 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)-2-naphthalen-2-yl-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