(2S,4S)-2-Hydroxymethyl-4-methoxymethoxy-piperidine-1-carboxylic acid tert-butyl ester | 332188-57-5

• 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,4S)-2-Hydroxymethyl-4-methoxymethoxy-piperidine-1-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2S,4S)-2-(hydroxymethyl)-4-(methoxymethoxy)piperidine-1-carboxylate
• CAS: 332188-57-5
• 化学式: C₁₃H₂₅NO₅
• 分子量: 275.345
• InChiKey: XXRZJSCCLWCZAA-QWRGUYRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  68.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,4S)-2-Hydroxymethyl-4-methoxymethoxy-piperidine-1-carboxylic acid tert-butyl ester 在 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 为溶剂， 生成 (2R,4R)-2-Formyl-4-methoxymethoxy-piperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of (2 R ,4 R )- and (2 S ,4 S )-4-hydroxypipecolic acid derivatives and (2 S ,4 S )-(−)-SS20846A

  摘要：

  Syntheses of protected derivatives of both enantiomers of trans-4-hydroxypipecolic acid (2) and the natural product (-)-SS20846A (3) were accomplished from vinylglycinols. Key transformations involved construction of the piperidine ring via ring-closing metathesis (Grubbs' catalyst) and installation of the 4-hydroxy substituent by Prevost reaction. X-Ray diffraction analyses conclusively established the regio- and stereochemistry of key intermediates. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02124-9
• 作为产物：
  描述：

  (S)-1,5,6,8a-tetrahydro-3H-oxazolo[3,4-a]pyridin-3-one 在 甲醇 、 potassium cyanide 、 sodium hydroxide 、 碘 、 镍 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙酸乙酯 、 苯 为溶剂， 反应 24.0h， 生成 (2S,4S)-2-Hydroxymethyl-4-methoxymethoxy-piperidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of (2 R ,4 R )- and (2 S ,4 S )-4-hydroxypipecolic acid derivatives and (2 S ,4 S )-(−)-SS20846A

  摘要：

  Syntheses of protected derivatives of both enantiomers of trans-4-hydroxypipecolic acid (2) and the natural product (-)-SS20846A (3) were accomplished from vinylglycinols. Key transformations involved construction of the piperidine ring via ring-closing metathesis (Grubbs' catalyst) and installation of the 4-hydroxy substituent by Prevost reaction. X-Ray diffraction analyses conclusively established the regio- and stereochemistry of key intermediates. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02124-9

文献信息

• Synthesis of (2 R ,4 R )- and (2 S ,4 S )-4-hydroxypipecolic acid derivatives and (2 S ,4 S )-(−)-SS20846A
  作者：Mark Sabat、Carl R Johnson

  DOI：10.1016/s0040-4039(00)02124-9

  日期：2001.2

  Syntheses of protected derivatives of both enantiomers of trans-4-hydroxypipecolic acid (2) and the natural product (-)-SS20846A (3) were accomplished from vinylglycinols. Key transformations involved construction of the piperidine ring via ring-closing metathesis (Grubbs' catalyst) and installation of the 4-hydroxy substituent by Prevost reaction. X-Ray diffraction analyses conclusively established the regio- and stereochemistry of key intermediates. (C) 2001 Elsevier Science Ltd. All rights reserved.