(2S,3S)-N-allyl-N-(tert-butoxycarbonyl)-3-amino-5-methyl-5-hexen-1,2-diol | 954379-00-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,3S)-N-allyl-N-(tert-butoxycarbonyl)-3-amino-5-methyl-5-hexen-1,2-diol
• 英文别名: tert-butyl N-[(2S,3S)-1,2-dihydroxy-5-methylhex-5-en-3-yl]-N-prop-2-enylcarbamate
• CAS: 954379-00-1
• 化学式: C₁₅H₂₇NO₄
• 分子量: 285.384
• InChiKey: ZXAIAADRWNOVMJ-QWHCGFSZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  70
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2S,3S)-N-allyl-N-(tert-butoxycarbonyl)-3-amino-5-methyl-5-hexen-1,2-diol 在 sodium periodate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 5.0h， 生成 tert-butyl N-[(2S)-4-methyl-1-oxopent-4-en-2-yl]-N-prop-2-enylcarbamate
  参考文献：
  名称：

  Enantioselective Synthesis of trans-4-Methylpipecolic Acid

  摘要：

  [GRAPHICS]An asymmetric synthesis for the preparation of both enantiomers of trans-methylpipecolic acids is described. It is based on Sharpless epoxidation as a chirality source, regioselective ring opening with allylamine, and ring-closing metathesis to construct the piperidine ring. The stereogenic center at C-4 is set by stereoselective hydrogenation that is directed by the alcohol functionality of an intermediate and proceeds with good diastereomeric control (trans/cis 16/1). Crystallization of the Boc-protected amino acid afforded the target products with excellent chemical (98% de) and enantiomeric purity (99% ee).

  DOI：

  10.1021/jo071220z
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 丙烯胺 、 (2R,3R)-2,3-epoxy-5-methyl-5-hexen-1-ol 在 lithium perchlorate 碳酸氢钠 作用下， 以 乙腈 、 甲醇 为溶剂， 反应 38.0h， 生成 (2S,3S)-N-allyl-N-(tert-butoxycarbonyl)-3-amino-5-methyl-5-hexen-1,2-diol 、 (2S,3R)-N-allyl-N-(tert-butoxycarbonyl)-2-amino-5-methyl-5-hexen-1,3-diol
  参考文献：
  名称：

  Enantioselective Synthesis of trans-4-Methylpipecolic Acid

  摘要：

  [GRAPHICS]An asymmetric synthesis for the preparation of both enantiomers of trans-methylpipecolic acids is described. It is based on Sharpless epoxidation as a chirality source, regioselective ring opening with allylamine, and ring-closing metathesis to construct the piperidine ring. The stereogenic center at C-4 is set by stereoselective hydrogenation that is directed by the alcohol functionality of an intermediate and proceeds with good diastereomeric control (trans/cis 16/1). Crystallization of the Boc-protected amino acid afforded the target products with excellent chemical (98% de) and enantiomeric purity (99% ee).

  DOI：

  10.1021/jo071220z

文献信息

• Enantioselective Synthesis of <i>trans</i>-4-Methylpipecolic Acid
  作者：Carlos Alegret、Ferran Santacana、Antoni Riera

  DOI：10.1021/jo071220z

  日期：2007.9.1

  [GRAPHICS]An asymmetric synthesis for the preparation of both enantiomers of trans-methylpipecolic acids is described. It is based on Sharpless epoxidation as a chirality source, regioselective ring opening with allylamine, and ring-closing metathesis to construct the piperidine ring. The stereogenic center at C-4 is set by stereoselective hydrogenation that is directed by the alcohol functionality of an intermediate and proceeds with good diastereomeric control (trans/cis 16/1). Crystallization of the Boc-protected amino acid afforded the target products with excellent chemical (98% de) and enantiomeric purity (99% ee).