(2S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-[(S)-2-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-ylidene)-2-hydroxy-1-methyl-ethylcarbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester | 177607-79-3

• 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)-2-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-ylidene)-2-hydroxy-1-methyl-ethylcarbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2S,4S)-4-[tert-butyl(dimethyl)silyl]oxy-2-[[(2S)-1-(2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)-1-hydroxypropan-2-yl]carbamoyl]pyrrolidine-1-carboxylate
• CAS: 177607-79-3
• 化学式: C₂₅H₄₂N₂O₉Si
• 分子量: 542.702
• InChiKey: YVHJOLCHZHLROW-JYJNAYRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.54
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  141
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-[(S)-2-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-ylidene)-2-hydroxy-1-methyl-ethylcarbamoyl]-pyrrolidine-1-carboxylic acid tert-butyl ester 在 盐酸 、 sodium tetrahydroborate 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 溶剂黄146 、 乙腈 为溶剂， 反应 14.33h， 生成 microcolin A
  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：

  二碳酸二叔丁酯 在 palladium on activated charcoal 2,6-二甲基吡啶 、 4-二甲氨基吡啶 、 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 为溶剂， 反应 85.25h， 生成 (2S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-[(S)-2-(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-ylidene)-2-hydroxy-1-methyl-ethylcarbamoyl]-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