3-Furanol, tetrahydro-5-methoxy-4-(2-propen-1-yl)-, (3S)- | 1260152-76-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧唑烯
• 英文名称: 3-Furanol, tetrahydro-5-methoxy-4-(2-propen-1-yl)-, (3S)-
• 英文别名: (3S)-5-methoxy-4-prop-2-enyloxolan-3-ol
• CAS: 1260152-76-8
• 化学式: C₈H₁₄O₃
• 分子量: 158.197
• InChiKey: GUKSIWJDELAMRA-ZUEIMRROSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-Furanol, tetrahydro-5-methoxy-4-(2-propen-1-yl)-, (3S)- 在 臭氧 、 二甲基硫 作用下， 以 二氯甲烷 为溶剂， 生成 2-[(4S)-4-hydroxy-2-methoxyoxolan-3-yl]acetaldehyde
  参考文献：
  名称：

  The efficient synthesis of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol and its isomers

  摘要：

  The stereoselective synthesis of all the possible stereoisomers of bis-tetrahydrofyran alcohol, a ligand used for obtaining HIV protease inhibitors including Darunavir 1 and Brecanavir 2 has been achieved. A key intermediate 4-pentenal 5 was obtained by employing a Wittig olefination-Claisen rearrangement protocol from D-glyceraldehyde derivative 3 as a source of chirality. The 4-pentenal was readily converted in the bis-THF alcohol moiety in three steps. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.08.005
• 作为产物：
  描述：

  甲醇 、 (S)-2-(1,4-dioxaspiro[4.5]-decan-2-yl)pent-4-enal 在 盐酸 作用下， 生成 3-Furanol, tetrahydro-5-methoxy-4-(2-propen-1-yl)-, (3S)-
  参考文献：
  名称：

  The efficient synthesis of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol and its isomers

  摘要：

  The stereoselective synthesis of all the possible stereoisomers of bis-tetrahydrofyran alcohol, a ligand used for obtaining HIV protease inhibitors including Darunavir 1 and Brecanavir 2 has been achieved. A key intermediate 4-pentenal 5 was obtained by employing a Wittig olefination-Claisen rearrangement protocol from D-glyceraldehyde derivative 3 as a source of chirality. The 4-pentenal was readily converted in the bis-THF alcohol moiety in three steps. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2010.08.005

文献信息

• The efficient synthesis of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol and its isomers
  作者：Mukund G. Kulkarni、Yunnus B. Shaikh、Ajit S. Borhade、Attrimuni P. Dhondge、Sanjay W. Chavhan、Mayur P. Desai、Deekshaputra R. Birhade、Nagorao R. Dhatrak、Ramesh Gannimani

  DOI：10.1016/j.tetasy.2010.08.005

  日期：2010.10

  The stereoselective synthesis of all the possible stereoisomers of bis-tetrahydrofyran alcohol, a ligand used for obtaining HIV protease inhibitors including Darunavir 1 and Brecanavir 2 has been achieved. A key intermediate 4-pentenal 5 was obtained by employing a Wittig olefination-Claisen rearrangement protocol from D-glyceraldehyde derivative 3 as a source of chirality. The 4-pentenal was readily converted in the bis-THF alcohol moiety in three steps. (C) 2010 Elsevier Ltd. All rights reserved.