benzyl (3S,4S,2'S)-4-[1-(tert-butyldiphenylsilyloxy)-2-propylamino]-2-methylhept-6-en-3-ylcarbamate | 1227182-87-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl (3S,4S,2'S)-4-[1-(tert-butyldiphenylsilyloxy)-2-propylamino]-2-methylhept-6-en-3-ylcarbamate
• 英文别名: benzyl N-[(3S,4S)-4-[[(2S)-1-[tert-butyl(diphenyl)silyl]oxypropan-2-yl]amino]-2-methylhept-6-en-3-yl]carbamate
• CAS: 1227182-87-7
• 化学式: C₃₅H₄₈N₂O₃Si
• 分子量: 572.863
• InChiKey: SUGGTRGQKLDUTI-RMFXYIPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.44
• 重原子数：
  41
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  59.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl (3S,4S,2'S)-4-[1-(tert-butyldiphenylsilyloxy)-2-propylamino]-2-methylhept-6-en-3-ylcarbamate 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97%的产率得到benzyl (3S,4S,2'S)-4-[1-(tert-butyldiphenylsilyloxy)-2-propylamino]-7-hydroxy-2-methyl-3-heptylcarbamate
  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：

  benzyl N-[(2S)-1-[(2S)-1-[tert-butyl(diphenyl)silyl]oxypropan-2-yl]imino-3-methylbutan-2-yl]carbamate 、 3-溴丙烯 在 cerium(III) chloride heptahydrate 、 锌 作用下， 以 四氢呋喃 为溶剂， 以51%的产率得到benzyl (3S,4S,2'S)-4-[1-(tert-butyldiphenylsilyloxy)-2-propylamino]-2-methylhept-6-en-3-ylcarbamate
  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