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 | 321921-84-0

• 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: 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
• 英文别名: [(2R,3R,4R,5S)-4-[tert-butyl(dimethyl)silyl]oxy-5-[(2S,3R)-3-[[tert-butyl(dimethyl)silyl]oxymethyl]oxiran-2-yl]-1,2-dihydroxyhexan-3-yl] benzoate
• CAS: 321921-84-0
• 化学式: C₂₈H₅₀O₇Si₂
• 分子量: 554.872
• InChiKey: ZEALSADSLIDLFA-MOJIEUQSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.38
• 重原子数：
  37
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  97.8
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  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 、 potassium hydride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (2R,4aR,6R,7S,8R,8aR)-6-[(R)-1-Benzyloxy-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-8-(tert-butyl-dimethyl-silanyloxy)-7-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine
  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,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 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 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
  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.