(2S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-((S)-3-methanesulfonyloxy-2-methyl-5-oxo-pyrrolidine-1-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester | 1053609-48-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-((S)-3-methanesulfonyloxy-2-methyl-5-oxo-pyrrolidine-1-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2S,4S)-4-[tert-butyl(dimethyl)silyl]oxy-2-[(2S)-2-methyl-3-methylsulfonyloxy-5-oxopyrrolidine-1-carbonyl]pyrrolidine-1-carboxylate
• CAS: 1053609-48-5
• 化学式: C₂₂H₄₀N₂O₈SSi
• 分子量: 520.72
• InChiKey: XPOUXEAGMLHLRS-RXMKTKRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.88
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  128
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-((S)-3-methanesulfonyloxy-2-methyl-5-oxo-pyrrolidine-1-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 生成 tert-butyl (2S,4S)-4-[tert-butyl(dimethyl)silyl]oxy-2-[(2S)-2-methyl-5-oxo-2H-pyrrole-1-carbonyl]pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Total Asymmetric Synthesis of the Potent Immunosuppressive Marine Natural Product Microcolin A

  摘要：

  The total asymmetric synthesis of the potent immunosuppressive compound microcolin A is reported, The synthesis establishes the absolute stereochemistry of microcolin A as C-36R, C-38R, and C-4S on the basis of the diastereoselective preparation of all four possible diastereomers of the lipid region (fragment A) and diastereoselective synthesis of fragment C starting from natural L-(S)-alanine. The strategy involves a convergent assemblage of three optically pure fragments and is amenable to chemical modifications to examine structural analogs for biological study.

  DOI：

  10.1021/jo952123l
• 作为产物：
  描述：

  顺式-4-羟基-L-脯氨酸 在 palladium on activated charcoal 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 异丙烯基氯甲酸酯 、 氢气 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 、 乙腈 为溶剂， 反应 93.25h， 生成 (2S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-((S)-3-methanesulfonyloxy-2-methyl-5-oxo-pyrrolidine-1-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Total Asymmetric Synthesis of the Potent Immunosuppressive Marine Natural Product Microcolin A

  摘要：

  The total asymmetric synthesis of the potent immunosuppressive compound microcolin A is reported, The synthesis establishes the absolute stereochemistry of microcolin A as C-36R, C-38R, and C-4S on the basis of the diastereoselective preparation of all four possible diastereomers of the lipid region (fragment A) and diastereoselective synthesis of fragment C starting from natural L-(S)-alanine. The strategy involves a convergent assemblage of three optically pure fragments and is amenable to chemical modifications to examine structural analogs for biological study.

  DOI：

  10.1021/jo952123l

文献信息

• Total Asymmetric Synthesis of the Potent Immunosuppressive Marine Natural Product Microcolin A
  作者：Carl P. Decicco、Paul Grover

  DOI：10.1021/jo952123l

  日期：1996.1.1

  The total asymmetric synthesis of the potent immunosuppressive compound microcolin A is reported, The synthesis establishes the absolute stereochemistry of microcolin A as C-36R, C-38R, and C-4S on the basis of the diastereoselective preparation of all four possible diastereomers of the lipid region (fragment A) and diastereoselective synthesis of fragment C starting from natural L-(S)-alanine. The strategy involves a convergent assemblage of three optically pure fragments and is amenable to chemical modifications to examine structural analogs for biological study.