(4R,5R)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-dihydro-furan-2-one | 949013-62-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (4R,5R)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-dihydro-furan-2-one
• 英文别名: (4R,5R)-5-[2-[tert-butyl(diphenyl)silyl]oxyethyl]-4-hydroxyoxolan-2-one
• CAS: 949013-62-1
• 化学式: C₂₂H₂₈O₄Si
• 分子量: 384.547
• InChiKey: VCGKVJMMOQZTAW-WOJBJXKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.63
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4R,5R)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-dihydro-furan-2-one 、 2,2,2-三氯代亚氨逐乙酸-4-甲氧基苄酯 在 三氟化硼乙醚 作用下， 生成 (4R,5R)-5-[2-[tert-butyl(diphenyl)silyl]oxyethyl]-4-[(4-methoxyphenyl)methoxy]oxolan-2-one
  参考文献：
  名称：

  Improved synthesis of the polyhydroxylated central part of phoslactomycin B

  摘要：

  A new approach to the C(7)-C(13) intermediate for the synthesis of phoslactomycin B was investigated. Asymmetric dihydroxylation of the beta,gamma-unsaturated ester proceeded cleanly to afford the beta-hydroxyl-gamma-lactone with 97.6% ee, which upon protection as the PMB ether followed by hydride reduction furnished a diol. After selective protection of the prim-OH, oxidation of the see-OH and chelation-controlled addition of CH2=CHMgBr afforded the C(7)-C(11) segment. Later on, the C(11) stereocentre was constructed by the asymmetric transfer hydrogenation using the Noyori catalyst. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.06.058
• 作为产物：
  描述：

  4-((tert-butyldiphenylsilyl)oxy)butanal 在 AD-mix-α 、 甲基磺酰胺 、 三乙胺 作用下， 以 水 、 叔丁醇 为溶剂， 反应 20.0h， 生成 (4R,5R)-5-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-4-hydroxy-dihydro-furan-2-one
  参考文献：
  名称：

  Stereoselective Syntheses of Rolliniastatin 1, Rollimembrin, and Membranacin

  摘要：

  A radical cyclization of beta-alkoxyvinyl sulfoxides-Pummerer rearrangement-allylation protocol was successfully applied to the synthesis of the threo/cis/threo/cis/erythro bis-oxolane moiety in rolliniastatin 1 (1), rollimembrin (2), and membranacin (3).

  DOI：

  10.1021/ja0526867

文献信息

• Stereoselective Syntheses of Rolliniastatin 1, Rollimembrin, and Membranacin
  作者：Gyochang Keum、Cheol Hee Hwang、Soon Bang Kang、Youseung Kim、Eun Lee

  DOI：10.1021/ja0526867

  日期：2005.7.1

  A radical cyclization of beta-alkoxyvinyl sulfoxides-Pummerer rearrangement-allylation protocol was successfully applied to the synthesis of the threo/cis/threo/cis/erythro bis-oxolane moiety in rolliniastatin 1 (1), rollimembrin (2), and membranacin (3).
• Improved synthesis of the polyhydroxylated central part of phoslactomycin B
  作者：Hisato Nonaka、Noriaki Maeda、Yuichi Kobayashi

  DOI：10.1016/j.tetlet.2007.06.058

  日期：2007.8

  A new approach to the C(7)-C(13) intermediate for the synthesis of phoslactomycin B was investigated. Asymmetric dihydroxylation of the beta,gamma-unsaturated ester proceeded cleanly to afford the beta-hydroxyl-gamma-lactone with 97.6% ee, which upon protection as the PMB ether followed by hydride reduction furnished a diol. After selective protection of the prim-OH, oxidation of the see-OH and chelation-controlled addition of CH2=CHMgBr afforded the C(7)-C(11) segment. Later on, the C(11) stereocentre was constructed by the asymmetric transfer hydrogenation using the Noyori catalyst. (c) 2007 Elsevier Ltd. All rights reserved.