(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 | 251319-67-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: (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
• CAS: 251319-67-2
• 化学式: C₂₈H₅₀O₆Si₂
• 分子量: 538.872
• InChiKey: HEMCODQOXCMUMT-NXQKNFRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.28
• 重原子数：
  36.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  66.38
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (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 在 吡啶 、 草酰氯 、 potassium hydride 、 氟化氢吡啶 、 二甲基亚砜 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (S)-1-Benzyloxy-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]-propan-2-one
  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：

  Benzoic acid (1R,2R,3S)-2-(tert-butyl-dimethyl-silanyloxy)-3-[(2S,3R)-3-(tert-butyl-dimethyl-silanyloxymethyl)-oxiranyl]-1-((R)-1,2-dihydroxy-ethyl)-butyl ester 在 camphor-10-sulfonic acid 、 二异丁基氢化铝 作用下， 以 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