(2S,3R,3aS,4R,6R)-4,6-Bis-(tert-butyl-dimethyl-silanyloxy)-hexahydro-isoxazolo[2,3-a]pyridine-2,3-dicarboxylic acid dimethyl ester | 519189-09-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (2S,3R,3aS,4R,6R)-4,6-Bis-(tert-butyl-dimethyl-silanyloxy)-hexahydro-isoxazolo[2,3-a]pyridine-2,3-dicarboxylic acid dimethyl ester
• 英文别名: dimethyl (2S,3R,3aS,4R,6R)-4,6-bis[[tert-butyl(dimethyl)silyl]oxy]-3,3a,4,5,6,7-hexahydro-2H-[1,2]oxazolo[2,3-a]pyridine-2,3-dicarboxylate
• CAS: 519189-09-4
• 化学式: C₂₃H₄₅NO₇Si₂
• 分子量: 503.784
• InChiKey: LGWIAZGOKOPXNG-NNIGNNQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.12
• 重原子数：
  33
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  83.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (2S,3R,3aS,4R,6R)-4,6-Bis-(tert-butyl-dimethyl-silanyloxy)-hexahydro-isoxazolo[2,3-a]pyridine-2,3-dicarboxylic acid dimethyl ester 、 alkaline earth salt of/the/ methylsulfuric acid 在 palladium dihydroxide 作用下， 以88%的产率得到(1R,2R,6R,8R,8aS)-6,8-Bis-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-3-oxo-octahydro-indolizine-1-carboxylic acid methyl ester
  参考文献：
  名称：

  A new nitrone from C2 symmetric piperidine for the synthesis of hydroxylated indolizidinone

  摘要：

  The oxidation of a C-2 symmetric piperidine, obtained through a ring enlargement process of the enantiopure protected (4R)-hydroxy-(2S)-hydroxymethyl pyrrolidine, is reported. Oxidation with C-phenyl-N-phenylsulfonyloxaziridine afforded the corresponding nitrone that is too unstable for isolation and which reacted in situ with dimethyl maleate. The major adduct was transformed to the corresponding protected dihydroxyindolizidinone. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02336-5
• 作为产物：
  描述：

  (3R,5R)-3,5-di[(tert-butyldimethylsilyl)oxy]-piperidine 反应 20.0h， 生成 (2S,3R,3aS,4R,6R)-4,6-Bis-(tert-butyl-dimethyl-silanyloxy)-hexahydro-isoxazolo[2,3-a]pyridine-2,3-dicarboxylic acid dimethyl ester
  参考文献：
  名称：

  A new nitrone from C2 symmetric piperidine for the synthesis of hydroxylated indolizidinone

  摘要：

  The oxidation of a C-2 symmetric piperidine, obtained through a ring enlargement process of the enantiopure protected (4R)-hydroxy-(2S)-hydroxymethyl pyrrolidine, is reported. Oxidation with C-phenyl-N-phenylsulfonyloxaziridine afforded the corresponding nitrone that is too unstable for isolation and which reacted in situ with dimethyl maleate. The major adduct was transformed to the corresponding protected dihydroxyindolizidinone. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02336-5

文献信息

• A new nitrone from C2 symmetric piperidine for the synthesis of hydroxylated indolizidinone
  作者：Alberto Brandi、Stefano Cicchi、Valentina Paschetta、Domingo Gomez Pardo、Janine Cossy

  DOI：10.1016/s0040-4039(02)02336-5

  日期：2002.12

  The oxidation of a C-2 symmetric piperidine, obtained through a ring enlargement process of the enantiopure protected (4R)-hydroxy-(2S)-hydroxymethyl pyrrolidine, is reported. Oxidation with C-phenyl-N-phenylsulfonyloxaziridine afforded the corresponding nitrone that is too unstable for isolation and which reacted in situ with dimethyl maleate. The major adduct was transformed to the corresponding protected dihydroxyindolizidinone. (C) 2002 Elsevier Science Ltd. All rights reserved.