(4R,5R)-5-((S)-3-Azido-1-methyl-propyl)-4-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester | 192129-54-7

• 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: (4R,5R)-5-((S)-3-Azido-1-methyl-propyl)-4-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
• CAS: 192129-54-7
• 化学式: C₃₁H₄₆N₄O₄Si
• 分子量: 566.816
• InChiKey: UAODGURHDWQMKT-HUROMRQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.64
• 重原子数：
  40.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  96.76
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (4R,5R)-5-((S)-3-Azido-1-methyl-propyl)-4-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 在 palladium on activated charcoal sodium hydroxide 、 四丁基氟化铵 、 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 21.08h， 生成 (4R,5R)-5-((S)-3-Benzyloxycarbonylamino-1-methyl-propyl)-4-methanesulfonyloxymethyl-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Formal synthesis of an unusual amino acid component of cyclosporin, involving stereocontrolled nucleophilic 1,4-addition

  摘要：

  A syn-(2R)-amino-1,3,4-butanetriol derivative, readily available from D-isoascorbic acid, was utilized for the synthesis of MeBmt found in the immunosuppressive undecacyclopeptide cyclosporin. This new strategy involves diastereoselective nucleophilic 1,4-addition of lithium dimethylcuprate to a chiral alpha,beta-unsaturated aldehyde, and elaboration of the terminal double bond, by Takai or Wittig method for the MeBmt or its 6Z-isomer, respectively. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00164-x
• 作为产物：
  描述：

  tert-butyl (4R,5R)-4-[[tert-butyl(diphenyl)silyl]oxymethyl]-2,2-dimethyl-5-[(E)-3-oxoprop-1-enyl]-1,3-oxazolidine-3-carboxylate 在 镍 2,6-二甲基吡啶 、 copper(l) iodide 、 氢气 、 N,N,N',N'-四甲基胍叠氮化物 作用下， 以 乙醇 、 氯仿 为溶剂， -50.0~-30.0 ℃ 、303.98 kPa 条件下， 反应 6.25h， 生成 (4R,5R)-5-((S)-3-Azido-1-methyl-propyl)-4-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Formal synthesis of an unusual amino acid component of cyclosporin, involving stereocontrolled nucleophilic 1,4-addition

  摘要：

  A syn-(2R)-amino-1,3,4-butanetriol derivative, readily available from D-isoascorbic acid, was utilized for the synthesis of MeBmt found in the immunosuppressive undecacyclopeptide cyclosporin. This new strategy involves diastereoselective nucleophilic 1,4-addition of lithium dimethylcuprate to a chiral alpha,beta-unsaturated aldehyde, and elaboration of the terminal double bond, by Takai or Wittig method for the MeBmt or its 6Z-isomer, respectively. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00164-x