cis-4-benzyloxy-2,3-epoxybutyl tosylate | 113426-91-8

• 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: cis-4-benzyloxy-2,3-epoxybutyl tosylate
• 英文别名: [(2S,3R)-3-(phenylmethoxymethyl)oxiran-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 113426-91-8
• 化学式: C₁₈H₂₀O₅S
• 分子量: 348.42
• InChiKey: BFDSNKKZNNGYAI-MSOLQXFVSA-N

物化性质

• 沸点：
  504.4±30.0 °C(Predicted)
• 密度：
  1.249±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  73.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  cis-4-benzyloxy-2,3-epoxybutyl tosylate 在 1-庚基锂 、 potassium iodide 作用下， 以 六甲基磷酰三胺 、 乙醚 、 正己烷 、 丙酮 为溶剂， 反应 98.0h， 生成 (2R)-1-(benzyloxy)but-3-en-2-ol
  参考文献：
  名称：

  Preparation et utilisation d'un synthon comportant un epoxyde chiral

  摘要：

  DOI：

  10.1016/s0040-4020(01)86875-7
• 作为产物：
  描述：

  顺-4-苄氧基-2-丁烯-1-醇 在 吡啶 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 33.0h， 生成 cis-4-benzyloxy-2,3-epoxybutyl tosylate
  参考文献：
  名称：

  Useful base promoted elaborations of oxiranyl ethers

  摘要：

  Functionalized oxiranyl ethers can be regio- and stereoselectively converted into hydroxy oxetanes or cis-diols by treatment with organometallic bases. These two rearrangements can be conveniently carried out either using different reaction conditions starting from the oxirane or in two consecutive steps from the oxirane via the oxetane. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00790-6

文献信息

• One-pot transformation of p-toluenesulfonates of 2,3-epoxy alcohols into allyic alcohols
  作者：Hiromu Habashita、Takeshi Kawasaki、Masako Akaji、Hirokazu Tamamura、Tetsutaro Kimachi、Nobutaka Fujii、Toshiro Ibuka

  DOI：10.1016/s0040-4039(97)10208-8

  日期：1997.12

  efficient method for the synthesis of synthetically useful non-racemic allylic alcohols from 4-methylbenzenesulfonates of non-racemic 2,3-epoxy alcohols is described. Satisfactory yields are obtained by treatment of 4-methylbenzenesulfonates of non-racemic 2,3-epoxy alcohols with potassium iodide followed by zinc powder and ammonium chloride in a one-pot manner. The method has been successfully applied to

  描述了一种由非外消旋2，3-环氧醇的4-甲基苯磺酸酯合成合成有用的非外消旋烯丙基醇的简便有效的方法。通过用碘化钾，然后一锅法用锌粉和氯化铵处理非外消旋2,3-环氧醇的4-甲基苯磺酸盐，获得令人满意的收率。该方法已成功应用于C 30 30C 37葡萄球菌的关键构件的合成。
• Efficient, scalable kinetic resolution of cis-4-benzyloxy-2,3-epoxybutanol
  作者：Ferenc Faigl、Angelika Thurner、Melinda Battancs、Ferenc Farkas、László Poppe、Viktória Bódai、Ildikó Kmecz、Béla Simándi

  DOI：10.1016/j.tetasy.2005.09.029

  日期：2005.11

  A new enzyme catalysed kinetic resolution of cis-4-benzyloxy-2,3-epoxybutanol has been reported. Efficient, scalable separation of the optically active alcohol from its ester derivative has been solved with liquid-liquid and solid-liquid extraction methods using commercial organic solvents and supercritical carbon dioxide. cis-4-Benzyloxy-2,3-epoxy-1-butanol enantiomers were applied for the enantio selective synthesis of (2S,3S,1'S)- and (2R,3R,1'R)-3-[2'-(dibenzylamino)-1'-hydroxyethyl]-2-phenyloxetane. (c) 2005 Elsevier Ltd. All rights reserved.
• Balmer, Ethnie; Germain, Andrew; Jackson, William P., Journal of the Chemical Society. Perkin transactions I, 1993, # 4, p. 399 - 400
  作者：Balmer, Ethnie、Germain, Andrew、Jackson, William P.、Lygo, Barry

  DOI：——

  日期：——
• SOULIE, J.;LAMPILAS, M.;LALLEMAND, J. Y., TETRAHEDRON, 43,(1987) N 12, 2701-2708
  作者：SOULIE, J.、LAMPILAS, M.、LALLEMAND, J. Y.

  DOI：——

  日期：——
• Useful base promoted elaborations of oxiranyl ethers
  作者：Angelika Thurner、Ferenc Faigl、László Tőke、Alessandro Mordini、Michela Valacchi、Gianna Reginato、Gábor Czira

  DOI：10.1016/s0040-4020(01)00790-6

  日期：2001.9

  Functionalized oxiranyl ethers can be regio- and stereoselectively converted into hydroxy oxetanes or cis-diols by treatment with organometallic bases. These two rearrangements can be conveniently carried out either using different reaction conditions starting from the oxirane or in two consecutive steps from the oxirane via the oxetane. (C) 2001 Elsevier Science Ltd. All rights reserved.