(R)-1-(1,2-dihydroxyethyl)cyclopropyl methanesulfonate | 1156508-41-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: (R)-1-(1,2-dihydroxyethyl)cyclopropyl methanesulfonate
• 英文别名: [1-[(1R)-1,2-dihydroxyethyl]cyclopropyl] methanesulfonate
• CAS: 1156508-41-6
• 化学式: C₆H₁₂O₅S
• 分子量: 196.224
• InChiKey: BJLUODIISUTGHF-RXMQYKEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  92.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-1-(1,2-dihydroxyethyl)cyclopropyl methanesulfonate 、 对甲苯磺酰氯 在 二正丁基氧化锡 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以93%的产率得到(R)-2-hydroxy-2-(1-(methylsulfonyloxy)cyclopropyl)ethyl 4-methylbenzenesulfonate
  参考文献：
  名称：

  A cyclopropanol approach to the synthesis of both enantiomers of the C13–C21 fragment of epothilones

  摘要：

  Efficient syntheses of both enantiomers of the C13-C21 fragment of epothilone molecules have been performed by use of enantiomeric oxiranyl-substituted cyclopropylsulfonates as key intermediates. The latter were obtained by the cyclopropanation of easily available (R)-methyl 2,3-O-isopropylideneglycerate and subsequent manipulation of the functional groups. Asymmetric allylation of 1-formylcyclopropyl pivalate led to an alternative precursor of the target compounds with moderate enantioselectivity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.02.003
• 作为产物：
  描述：

  (R)-1-(2,2-dimethyl-1,3-dioxolan-4-yl)cyclopropyl methanesulfonate 在 乙醇 、 4-甲基苯磺酸吡啶 作用下， 反应 2.0h， 以91%的产率得到(R)-1-(1,2-dihydroxyethyl)cyclopropyl methanesulfonate
  参考文献：
  名称：

  A cyclopropanol approach to the synthesis of both enantiomers of the C13–C21 fragment of epothilones

  摘要：

  Efficient syntheses of both enantiomers of the C13-C21 fragment of epothilone molecules have been performed by use of enantiomeric oxiranyl-substituted cyclopropylsulfonates as key intermediates. The latter were obtained by the cyclopropanation of easily available (R)-methyl 2,3-O-isopropylideneglycerate and subsequent manipulation of the functional groups. Asymmetric allylation of 1-formylcyclopropyl pivalate led to an alternative precursor of the target compounds with moderate enantioselectivity. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.02.003

文献信息

• A cyclopropanol approach to the synthesis of both enantiomers of the C13–C21 fragment of epothilones
  作者：Alaksiej L. Hurski、Nikolai A. Sokolov、Oleg G. Kulinkovich

  DOI：10.1016/j.tet.2009.02.003

  日期：2009.4

  Efficient syntheses of both enantiomers of the C13-C21 fragment of epothilone molecules have been performed by use of enantiomeric oxiranyl-substituted cyclopropylsulfonates as key intermediates. The latter were obtained by the cyclopropanation of easily available (R)-methyl 2,3-O-isopropylideneglycerate and subsequent manipulation of the functional groups. Asymmetric allylation of 1-formylcyclopropyl pivalate led to an alternative precursor of the target compounds with moderate enantioselectivity. (C) 2009 Elsevier Ltd. All rights reserved.