{(2R,3S)-3-[(Z)-(1R,2S)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-pent-3-enyl]-oxiranyl}-methanol | 251319-58-1

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: {(2R,3S)-3-[(Z)-(1R,2S)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-pent-3-enyl]-oxiranyl}-methanol
• 英文别名: [(2R,3S)-3-[(Z,1R,2S)-1,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methylpent-3-enyl]oxiran-2-yl]methanol
• CAS: 251319-58-1
• 化学式: C₂₁H₄₄O₄Si₂
• 分子量: 416.749
• InChiKey: WGQNAUKFMBRCCQ-LRYVBVNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.35
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  {(2R,3S)-3-[(Z)-(1R,2S)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-pent-3-enyl]-oxiranyl}-methanol 在 titanium(IV) isopropylate 、 camphor-10-sulfonic acid 、 二甲基二环氧乙烷 、 二异丁基氢化铝 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 (R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-[(2R,4aR,6R,7S,8R,8aR)-8-(tert-butyl-dimethyl-silanyloxy)-7-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-ethanol
  参考文献：
  名称：

  Asymmetric synthesis of the F-pyran fragment of the altohyrtins

  摘要：

  The asymmetric synthesis of a differentially protected F-pyran ring of the altohyrtins has been achieved through an intramolecular cyclisation of a C-43 hydroxyl group onto a C-38-C-39 epoxide. Absolute stereochemistry was derived from an Evans boron aldol to control C-40 and C-41, the C-42-C-43 hydroxyl stereocentres from a Sharpless (-)-diethyl tartrate controlled epoxidation and the remaining stereocentres from substrate controlled diastereoselection. (C) 1999 Elsevier Science: Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01481-1
• 作为产物：
  描述：

  (2R,3R,4E)-2-methyl-3-(tert-butyldimethylsilyloxy)-6-(phenylmethoxy)hex-4-en-1-al 在 titanium(IV) isopropylate 咪唑 、 叔丁基过氧化氢 、 18-冠醚-6 、 4 A molecular sieve 、 双(三甲基硅烷基)氨基钾 、 LiDBB 、 (-)-diethyl tartrate 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 {(2R,3S)-3-[(Z)-(1R,2S)-1,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methyl-pent-3-enyl]-oxiranyl}-methanol
  参考文献：
  名称：

  Asymmetric synthesis of the F-pyran fragment of the altohyrtins

  摘要：

  The asymmetric synthesis of a differentially protected F-pyran ring of the altohyrtins has been achieved through an intramolecular cyclisation of a C-43 hydroxyl group onto a C-38-C-39 epoxide. Absolute stereochemistry was derived from an Evans boron aldol to control C-40 and C-41, the C-42-C-43 hydroxyl stereocentres from a Sharpless (-)-diethyl tartrate controlled epoxidation and the remaining stereocentres from substrate controlled diastereoselection. (C) 1999 Elsevier Science: Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)01481-1

文献信息

• Asymmetric synthesis of the F-pyran fragment of the altohyrtins
  作者：James C. Anderson、Benjamin P. McDermott

  DOI：10.1016/s0040-4039(99)01481-1

  日期：1999.9

  The asymmetric synthesis of a differentially protected F-pyran ring of the altohyrtins has been achieved through an intramolecular cyclisation of a C-43 hydroxyl group onto a C-38-C-39 epoxide. Absolute stereochemistry was derived from an Evans boron aldol to control C-40 and C-41, the C-42-C-43 hydroxyl stereocentres from a Sharpless (-)-diethyl tartrate controlled epoxidation and the remaining stereocentres from substrate controlled diastereoselection. (C) 1999 Elsevier Science: Ltd. All rights reserved.