tert-butyl (2S,4'S,5'S)-2-[5-(benzyloxycarbonylamino)-6-methylhept-1-en-4-ylamino]-3-phenypropanoate | 1227183-11-0

• 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: tert-butyl (2S,4'S,5'S)-2-[5-(benzyloxycarbonylamino)-6-methylhept-1-en-4-ylamino]-3-phenypropanoate
• 英文别名: tert-butyl (2S)-2-[[(4S,5S)-6-methyl-5-(phenylmethoxycarbonylamino)hept-1-en-4-yl]amino]-3-phenylpropanoate
• CAS: 1227183-11-0
• 化学式: C₂₉H₄₀N₂O₄
• 分子量: 480.648
• InChiKey: WLIPZYCVGWCMNK-GSDHBNRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  35
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S,4'S,5'S)-2-[5-(benzyloxycarbonylamino)-6-methylhept-1-en-4-ylamino]-3-phenypropanoate 在 9-硼双环[3.3.1]壬烷 、 双氧水 、 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以94%的产率得到tert-butyl (2S,4'S,5'S)-2-[5-(benzyloxycarbonylamino)-1-hydroxy-6-methyl-4-heptylamino]-3-phenylpropanoate
  参考文献：
  名称：

  Addition of allylzinc to α-amino acid-derived imines: synthesis of diamino alcohols by hydroboration

  摘要：

  Imines obtained by condensation of Z-protected or Boc-protected alpha-amino aldehydes with alpha-amino tert-butyl esters or with O-silyl-protected amino alcohols were reacted with preformed allyl zinc yielding homoallylamines with yields around 50% and selectivities ranging from 50: 50 to 90: 10. Hydroboration of the terminal double bond furnished diamino alcohols with yields up to 97%. The configuration of the substrates was determined by X-ray-crystallographic analysis of a hydroboration product and comparison of physical data.

  DOI：

  10.1007/s00706-009-0239-y
• 作为产物：
  描述：

  tert-butyl (2S)-2-[[(2S)-3-methyl-2-(phenylmethoxycarbonylamino)butylidene]amino]-3-phenylpropanoate 、 3-溴丙烯 在 cerium(III) chloride heptahydrate 、 锌 作用下， 以 四氢呋喃 为溶剂， 以53%的产率得到tert-butyl (2S,4'S,5'S)-2-[5-(benzyloxycarbonylamino)-6-methylhept-1-en-4-ylamino]-3-phenypropanoate
  参考文献：
  名称：

  Addition of allylzinc to α-amino acid-derived imines: synthesis of diamino alcohols by hydroboration

  摘要：

  Imines obtained by condensation of Z-protected or Boc-protected alpha-amino aldehydes with alpha-amino tert-butyl esters or with O-silyl-protected amino alcohols were reacted with preformed allyl zinc yielding homoallylamines with yields around 50% and selectivities ranging from 50: 50 to 90: 10. Hydroboration of the terminal double bond furnished diamino alcohols with yields up to 97%. The configuration of the substrates was determined by X-ray-crystallographic analysis of a hydroboration product and comparison of physical data.

  DOI：

  10.1007/s00706-009-0239-y