(2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(2,6-dioxo-tetrahydro-pyran-4-yl)-pyrrolidine-1-carboxylic acid benzyl ester | 1025906-04-0

• 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: (2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(2,6-dioxo-tetrahydro-pyran-4-yl)-pyrrolidine-1-carboxylic acid benzyl ester
• 英文别名: benzyl (2S,4R)-4-[tert-butyl(dimethyl)silyl]oxy-2-(2,6-dioxooxan-4-yl)pyrrolidine-1-carboxylate
• CAS: 1025906-04-0
• 化学式: C₂₃H₃₃NO₆Si
• 分子量: 447.604
• InChiKey: UMTATGVDNBYFES-MOPGFXCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.27
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(2,6-dioxo-tetrahydro-pyran-4-yl)-pyrrolidine-1-carboxylic acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 4-[(2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-pyrrolidin-2-yl]-dihydro-pyran-2,6-dione
  参考文献：
  名称：

  An efficient synthesis of the side chain intermediate of BO-2502A, a new 1β-methyl carbapenem, via diastereoselective lactamization as a key step

  摘要：

  The BO-2502A side chain intermediate 3 was prepared via the diastereoselective lactamization of the in situ prepared amino diacid anhydride 14 as a key step. The diastereoselectivity of this step was found to be 53:1 (96% de). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00007-6
• 作为产物：
  描述：

  3-[(2S,4R)-1-Benzyloxycarbonyl-4-(tert-butyl-dimethyl-silanyloxy)-pyrrolidin-2-yl]-pentanedioic acid 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 生成 (2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(2,6-dioxo-tetrahydro-pyran-4-yl)-pyrrolidine-1-carboxylic acid benzyl ester
  参考文献：
  名称：

  An efficient synthesis of the side chain intermediate of BO-2502A, a new 1β-methyl carbapenem, via diastereoselective lactamization as a key step

  摘要：

  The BO-2502A side chain intermediate 3 was prepared via the diastereoselective lactamization of the in situ prepared amino diacid anhydride 14 as a key step. The diastereoselectivity of this step was found to be 53:1 (96% de). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00007-6