(2S)-3-phthalimido-2-((1R)-1-tert-butyldimethylsilyloxyethyl)propionic acid benzyl ester | 178395-72-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: (2S)-3-phthalimido-2-((1R)-1-tert-butyldimethylsilyloxyethyl)propionic acid benzyl ester
• 英文别名: benzyl (2S,3R)-3-[tert-butyl(dimethyl)silyl]oxy-2-[(1,3-dioxoisoindol-2-yl)methyl]butanoate
• CAS: 178395-72-7
• 化学式: C₂₆H₃₃NO₅Si
• 分子量: 467.637
• InChiKey: SRZCFCYDWRNVMU-GCJKJVERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.05
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  72.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S)-3-phthalimido-2-((1R)-1-tert-butyldimethylsilyloxyethyl)propionic acid benzyl ester 在 palladium on activated charcoal 2,2'-二硫二吡啶 、 氢气 、 一水合肼 、 三苯基膦 作用下， 以 甲醇 、 乙醇 、 乙腈 为溶剂， 25.0~60.0 ℃ 、101.33 kPa 条件下， 反应 29.0h， 生成 (1'R,3S)-3-<1'-<(tert-butyldimethylsilyl)oxy>ethyl>azetidin-2-one
  参考文献：
  名称：

  A novel synthesis of a key intermediate for penems and carbapenems utilizing lipase-catalyzed kinetic resolution

  摘要：

  Titanium enolate-mediated aldol reaction of N-phthaloyl-beta-alanyl-1, 3-benzoxazinone 5 with acetaldehyde gave the (+/-)-syn-aldol (+/-)-6 in a high yield with high diastereoselectivity. Lipase-catalyzed hydrolysis of the corresponding laurate (+/-)-7b furnished enantiomerically pure (2S, 3R)-N-(2-phthaloylaminomethyl-3-hydroxybutyryl)-1, 3-benzoxazinone 6 in 49% yield. Silylation of the hydroxy group of (29, 3R)-6 follwed by deprotection of the amino and carboxy groups gave the beta-amino acid derivative 9 which was transformed into the acetoxyazetidinone 3, a key intermediate of penems and carbapenems. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00132-2
• 作为产物：
  描述：

  lithium benzyloxide 、 2-[(2S,3R)-3-[tert-butyl(dimethyl)silyl]oxy-2-(2,2-diethyl-4-oxo-1,3-benzoxazine-3-carbonyl)butyl]isoindole-1,3-dione 以 甲苯 为溶剂， 反应 24.0h， 生成 (2S)-3-phthalimido-2-((1R)-1-tert-butyldimethylsilyloxyethyl)propionic acid benzyl ester
  参考文献：
  名称：

  A novel synthesis of a key intermediate for penems and carbapenems utilizing lipase-catalyzed kinetic resolution

  摘要：

  Titanium enolate-mediated aldol reaction of N-phthaloyl-beta-alanyl-1, 3-benzoxazinone 5 with acetaldehyde gave the (+/-)-syn-aldol (+/-)-6 in a high yield with high diastereoselectivity. Lipase-catalyzed hydrolysis of the corresponding laurate (+/-)-7b furnished enantiomerically pure (2S, 3R)-N-(2-phthaloylaminomethyl-3-hydroxybutyryl)-1, 3-benzoxazinone 6 in 49% yield. Silylation of the hydroxy group of (29, 3R)-6 follwed by deprotection of the amino and carboxy groups gave the beta-amino acid derivative 9 which was transformed into the acetoxyazetidinone 3, a key intermediate of penems and carbapenems. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0957-4166(96)00132-2

文献信息

• Process for preparing acetoxyazetidinone derivative and intermediate
  申请人：Tanabe Seiyaku Co., Ltd.

  公开号：US05831091A1

  公开（公告）日：1998-11-03

  An N-\x9b2-(1-hydroxyethyl)-3-oxopropyl!amine compound of the formula \x9bIII!: ##STR1## wherein Ring B represents a benzene ring which may be substituted; W represents oxygen atom or sulfur atom; Y represents oxygen atom, sulfur atom or N R.sup.0, R.sup.0 represents hydrogen atom or a substituent; Z represents a substituted methylene group which contains at least one chiral center; R.sup.5 represents an aralkyloxycarbonyl group or an alkoxycarbonyl group; R.sup.6 represents hydrogen atom, an aralkyl group, an acyloxy group, a tri-substituted silyloxy group or an alkoxy group; or both of R.sup.5 and R.sup.6 bond at their termini and combine with the adjacent nitrogen atom to form phthalimido group, and a process thereof are disclosed. Said compound \x9bIII! is useful as a starting compound of .beta.-lactam antibacterial agents.

  公式为III的N-\x9b2-(1-羟乙基)-3-氧代戊二酰基胺化合物：##STR1## 其中，环B代表可能被取代的苯环；W代表氧原子或硫原子；Y代表氧原子、硫原子或N R.sup.0，R.sup.0代表氢原子或取代基；Z代表含有至少一个手性中心的取代亚甲基基团；R.sup.5代表芳基烷氧羰基基团或烷氧羰基基团；R.sup.6代表氢原子、芳基烷基基团、酰氧基、三取代硅氧基或烷氧基；或者R.sup.5和R.sup.6在其末端结合并与相邻的氮原子结合形成邻苯二甲酰亚胺基团；公开了其制备过程。所述的化合物\x9bIII!可用作β-内酰胺类抗菌药物的起始化合物。
• A novel synthesis of a key intermediate for penems and carbapenems utilizing lipase-catalyzed kinetic resolution
  作者：Masahiko Seki、Toshiyuki Furutani、Tsutomu Miyake、Takeshi Yamanaka、Hiroshi Ohmizu

  DOI：10.1016/0957-4166(96)00132-2

  日期：1996.5

  Titanium enolate-mediated aldol reaction of N-phthaloyl-beta-alanyl-1, 3-benzoxazinone 5 with acetaldehyde gave the (+/-)-syn-aldol (+/-)-6 in a high yield with high diastereoselectivity. Lipase-catalyzed hydrolysis of the corresponding laurate (+/-)-7b furnished enantiomerically pure (2S, 3R)-N-(2-phthaloylaminomethyl-3-hydroxybutyryl)-1, 3-benzoxazinone 6 in 49% yield. Silylation of the hydroxy group of (29, 3R)-6 follwed by deprotection of the amino and carboxy groups gave the beta-amino acid derivative 9 which was transformed into the acetoxyazetidinone 3, a key intermediate of penems and carbapenems. Copyright (C) 1996 Elsevier Science Ltd