tert-butyl (2S,4'S,5'S)-2-[5-(benzyloxycarbonylamino)-1-hydroxy-6-methyl-4-heptylamino]-4-methylpentanoate | 1227183-25-6

• 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)-1-hydroxy-6-methyl-4-heptylamino]-4-methylpentanoate
• 英文别名: tert-butyl (2S)-2-[[(4S,5S)-1-hydroxy-6-methyl-5-(phenylmethoxycarbonylamino)heptan-4-yl]amino]-4-methylpentanoate
• CAS: 1227183-25-6
• 化学式: C₂₆H₄₄N₂O₅
• 分子量: 464.646
• InChiKey: UYPJLAGYCOWKTO-VABKMULXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  33
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  96.9
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S,4'S,5'S)-2-[5-(benzyloxycarbonylamino)-1-hydroxy-6-methyl-4-heptylamino]-4-methylpentanoate 在 4-二甲氨基吡啶 、 三乙胺 、 对甲苯磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以78%的产率得到tert-butyl (2S,2'S,1''S)-2-[2-(1-benzyloxycarbonylamino-2-methylpropyl)pyrrolidin-1-yl]-4-methylpentanoate
  参考文献：
  名称：

  γ-Lactam-containing peptidomimetics

  摘要：

  Protected diaminoalcohols obtained through allyl addition to alpha-amino acid-derived imines and subsequent hydroboration were used for the preparation of pyrrolidinones and pyrrolidines. Pyrrolidinones were synthesized with moderate yields by oxidation of the hydroxy function with tetrapropylammonium perruthenate/N-methylmorpholine-N-oxide and concomitant cyclization while pyrrolidines were synthesized in good yields by tosylation of the hydroxy group and subsequent intramolecular nucleophilic substitution. Thus accessible substrates were transferred into peptidomimetics by attachment of amino acid moieties at both termini using conventional peptide coupling strategies. Molecular mechanics optimizations suggest that these substrates preferentially adopt a turn conformation. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.05.099
• 作为产物：
  描述：

  tert-butyl (2S,4'S,5'S)-2-[5-(benzyloxycarbonylamino)-6-methylhept-1-en-4-ylamino]-4-methylpentanoate 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]-4-methylpentanoate
  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