(2S,3S)-(-)-1-(Tosyloxy)-2,3-epoxypentan | 117120-69-1

• 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: (2S,3S)-(-)-1-(Tosyloxy)-2,3-epoxypentan
• 英文别名: [(2S,3S)-3-ethyloxiran-2-yl]methyl 4-methylbenzenesulfonate
• CAS: 117120-69-1
• 化学式: C₁₂H₁₆O₄S
• 分子量: 256.323
• InChiKey: IAGCVENSXXIEMO-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  64.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S)-(-)-1-(Tosyloxy)-2,3-epoxypentan 在 2,6-二甲基吡啶 、 magnesium iodide 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 50.0h， 生成 Toluene-4-sulfonic acid (R)-2-(tert-butyl-dimethyl-silanyloxy)-pentyl ester
  参考文献：
  名称：

  Stereoselective synthesis of C15C24 and C25C30 fragments of dolabelides

  摘要：

  The stereocontrolled synthesis of a C15-C24 fragment of dolabelides is reported. The C19 and C21 hydroxyl-bearing stereocenters were installed using ruthenium-mediated asymmetric hydrogenations of cyclic hemiketal 4 and beta-keto ester 7. The C25-C30 portion of dolabelides was prepared as well by ring opening of chiral epoxy alcohol 12 to set up the C27 stereogenic center. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00110-2
• 作为产物：
  描述：

  ((2S,3S)-3-ethyloxiran-2-yl)methanol 、 对甲苯磺酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 反应 3.0h， 以92%的产率得到(2S,3S)-(-)-1-(Tosyloxy)-2,3-epoxypentan
  参考文献：
  名称：

  Wershofen, Stefan; Classen, Arnold; Scharf, Hans-Dieter, Liebigs Annalen der Chemie, 1989, p. 9 - 18

  摘要：

  DOI：

文献信息

• Ring opening of 2,3-epoxy 1-tosylates to halohydrins and subsequent elaboration to asymmetrical alcohols
  作者：Chiara Federici、Giuliana Righi、Leucio Rossi、Carlo Bonini、Lucia Chiummiento、Maria Funicello

  DOI：10.1016/s0040-4039(00)75820-5

  日期：1994.1

  2,3-epoxy alcohols-1-tosylates are regio and chemoselectively opened to the corresponding 3-halohydrins (I, Br, Cl): the reduction of the iodohydrins to the monoprotected diols and subsequent standard coupling of the tosyl group leads to a straightforward synthesis of optically active naturally occurring pheromones.
• WERSHOFEN, STEFAN;GLASS. EN, ARNOLD;SCHARF, HANS-DIETER, LIEBIGS ANN. CHEM.,(1989) N, C. 9-18
  作者：WERSHOFEN, STEFAN、GLASS. EN, ARNOLD、SCHARF, HANS-DIETER

  DOI：——

  日期：——
• Wershofen, Stefan; Classen, Arnold; Scharf, Hans-Dieter, Liebigs Annalen der Chemie, 1989, p. 9 - 18
  作者：Wershofen, Stefan、Classen, Arnold、Scharf, Hans-Dieter

  DOI：——

  日期：——
• Stereoselective synthesis of C15C24 and C25C30 fragments of dolabelides
  作者：Nicolas Desroy、Rémi Le Roux、Phannarath Phansavath、Lucia Chiummiento、Carlo Bonini、Jean-Pierre Genêt

  DOI：10.1016/s0040-4039(03)00110-2

  日期：2003.2

  The stereocontrolled synthesis of a C15-C24 fragment of dolabelides is reported. The C19 and C21 hydroxyl-bearing stereocenters were installed using ruthenium-mediated asymmetric hydrogenations of cyclic hemiketal 4 and beta-keto ester 7. The C25-C30 portion of dolabelides was prepared as well by ring opening of chiral epoxy alcohol 12 to set up the C27 stereogenic center. (C) 2003 Elsevier Science Ltd. All rights reserved.