(2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(2-methylcarbamoyl-acetyl)-pyrrolidine-1-carboxylic acid tert-butyl ester | 149814-42-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(2-methylcarbamoyl-acetyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
• 英文别名: (2S,4R)-N-tert-butoxycarbonyl-4-tert-butyldimethylsiloxy-2-[2-(N-methylcarbamoyl)-1-oxoethyl]pyrrolidine；tert-butyl (2S,4R)-4-[tert-butyl(dimethyl)silyl]oxy-2-[3-(methylamino)-3-oxopropanoyl]pyrrolidine-1-carboxylate
• CAS: 149814-42-6
• 化学式: C₁₉H₃₆N₂O₅Si
• 分子量: 400.591
• InChiKey: UWEUIDYYDYDJDD-KGLIPLIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.09
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(2-methylcarbamoyl-acetyl)-pyrrolidine-1-carboxylic acid tert-butyl ester 在 RuCl₂[(S)-BINAP] 、 氢气 、 三乙胺 作用下， 以 甲醇 为溶剂， 62.0 ℃ 、490.29 kPa 条件下， 反应 26.0h， 生成 (2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(1-hydroxy-2-methylcarbamoyl-ethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Diastereoselective synthesis of the key intermediate of the BO-2727 side chain

  摘要：

  The key intermediate of the BO-2727 side chain 3 was prepared diastereoselectively by two alternative methods: via the aldol reaction of (2S,4R)-N-Boc-tert-butyldimethylsilyloxyprolinal 5 with in-situ-generated ketene acetal 9 in the presence of TiCl4 (95% de) and via the catalytic hydrogenation of beta-keto amide 6i using (S)-BINAP-Ru as a catalyst (98% de). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00315-7
• 作为产物：
  描述：

  (2S,4R)-1-(叔丁氧羰基)-4-((叔丁基二甲基甲硅烷基)氧基)吡咯烷-2-羧酸 在 N,N'-羰基二咪唑 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.67h， 生成 (2S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-(2-methylcarbamoyl-acetyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Diastereoselective synthesis of the key intermediate of the BO-2727 side chain

  摘要：

  The key intermediate of the BO-2727 side chain 3 was prepared diastereoselectively by two alternative methods: via the aldol reaction of (2S,4R)-N-Boc-tert-butyldimethylsilyloxyprolinal 5 with in-situ-generated ketene acetal 9 in the presence of TiCl4 (95% de) and via the catalytic hydrogenation of beta-keto amide 6i using (S)-BINAP-Ru as a catalyst (98% de). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(97)00315-7

文献信息

• Aminoalkylpyrrolidinylthiocarbapenem derivatives
  申请人：Banyu Pharmaceutical Co., Ltd.

  公开号：US05550121A1

  公开（公告）日：1996-08-27

  A compound of the formula: ##STR1## wherein R.sup.1 is a hydrogen atom or a methyl group, R.sup.2 is a hydrogen atom or a negative charge, R.sup.3 is a hydrogen atom, a halogen atom, a hydroxyl group, a lower alkoxy group, a lower alkanoyloxy group, an amino group, an N-lower alkylamino group, an N,N-di-lower alkylamino group, a lower alkanoylamino group, an aroylamino group, a (lower alkylsulfonyl)amino group, a sulfamoylamino group, a cyano group, a nitro group, a group of --COOR.sup.4 (wherein R.sup.4 is a hydrogen atom or a lower alkyl group) or a group of --CON(R.sup.5)R.sup.6 (wherein each of R.sup.5 and R.sup.6 which may be the same or different, is a hydrogen atom or a lower alkyl group, or R.sup.5 and R.sup.6 form together with the adjacent nitrogen atom a heterocyclic group selected from the group consisting of an aziridinyl group, an azetidinyl group, a pyrrolidinyl group, a piperidyl group, a piperazinyl group, a 4-lower alkyl piperazinyl group and a morpholino group), A is a linear or branched lower alkylene group, X is a group of --N(R.sup.7)R.sup.8 (wherein each of R.sup.7 and R.sup.8 which may be the same or different, is a hydrogen atom or a lower alkyl group) or a group of --N.sup.+ (R.sup.9)(R.sup.10)R.sup.11 (wherein each of R.sup.9, R.sup.10 and R.sup.11 which may be the same or different, is a lower alkyl group), provided that when A is a linear lower alkylene group, R.sup.3 is other than a hydrogen atom; or a pharmaceutically acceptable salt or ester thereof.

  该化合物的式子为：##STR1## 其中R.sup.1是氢原子或甲基基团，R.sup.2是氢原子或负电荷，R.sup.3是氢原子、卤素原子、羟基、较低的烷氧基、较低的烷酰氧基、氨基、N-较低烷基氨基、N,N-二较低烷基氨基、较低烷酰氨基、芳酰氨基、(较低烷基磺酰)氨基、磺酰胺氨基、氰基、硝基、--COOR.sup.4（其中R.sup.4是氢原子或较低烷基）或--CON（R.sup.5）R.sup.6（其中R.sup.5和R.sup.6可以相同或不同，是氢原子或较低烷基，或R.sup.5和R.sup.6与相邻的氮原子一起形成从以下组成的杂环基团中选择的杂环基团：氮杂环羟胺基、氮杂环四元环基团、吡咯烷基团、哌啶基团、哌嗪基团、4-较低烷基哌嗪基团和吗啉基团），A是线性或支链状的较低烷基烷基链，X是--N（R.sup.7）R.sup.8（其中每个R.sup.7和R.sup.8可以相同或不同，是氢原子或较低烷基）或--N.sup.+（R.sup.9）（R.sup.10）R.sup.11（其中每个R.sup.9，R.sup.10和R.sup.11可以相同或不同，是较低烷基），但当A是线性较低烷基烷基链时，R.sup.3不是氢原子；或其药学上可接受的盐或酯。
• Diastereoselective synthesis of the key intermediate of the BO-2727 side chain
  作者：Norikazu Ohtake、Hideki Jona、Shigemitsu Okada、Osamu Okamoto、Yasuyuki Imai、Ryosuke Ushijima、Susumu Nakagawa

  DOI：10.1016/s0957-4166(97)00315-7

  日期：1997.9

  The key intermediate of the BO-2727 side chain 3 was prepared diastereoselectively by two alternative methods: via the aldol reaction of (2S,4R)-N-Boc-tert-butyldimethylsilyloxyprolinal 5 with in-situ-generated ketene acetal 9 in the presence of TiCl4 (95% de) and via the catalytic hydrogenation of beta-keto amide 6i using (S)-BINAP-Ru as a catalyst (98% de). (C) 1997 Elsevier Science Ltd.