(4S,5R,6S,1'S)-5-acetoxy-4-benzyl-6-<1-<<(benzyloxy)carbonyl>amino>-2-phenylethyl>-3,4,5,6-tetrahydro-2H-1,3-oxazin-2-one | 143747-09-5

• 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: (4S,5R,6S,1'S)-5-acetoxy-4-benzyl-6-<1-<<(benzyloxy)carbonyl>amino>-2-phenylethyl>-3,4,5,6-tetrahydro-2H-1,3-oxazin-2-one
• 英文别名: (4S,5R,6S)-tetrahydro-5-acetyloxy-6-((S)-1-benzyloxycarbonylamino-2-phenylethyl)-4-phenylmethyl-2H-1,3-oxazin-2-one；(4S,5R,6S,1'S)-5-acetoxy-4-benzyl-6-(1-{[(benzyloxy)carbonyl]amino}-2-phenylethyl)-3,4,5,6-tetrahydro-2H-1,3-oxazin-2-one；[(4S,5R,6S)-4-benzyl-2-oxo-6-[(1S)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]-1,3-oxazinan-5-yl] acetate
• CAS: 143747-09-5
• 化学式: C₂₉H₃₀N₂O₆
• 分子量: 502.567
• InChiKey: CTATWOORDMSZDQ-NFGXINMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4S,5R,6S,1'S)-5-acetoxy-4-benzyl-6-<1-<<(benzyloxy)carbonyl>amino>-2-phenylethyl>-3,4,5,6-tetrahydro-2H-1,3-oxazin-2-one 在 barium dihydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 11.0h， 以80%的产率得到2S,3R,4S,5S-2,5-diamino-3,4-dihydroxy-1,6-diphenyl hexane
  参考文献：
  名称：

  Stereocontrolled synthesis of C2-symmetric and pseudo-C2-symmetric diamino alcohols and diols for use in HIV protease inhibitors

  摘要：

  The stereocontrolled syntheses of dibenzyldiamino alcohol 1 and dibenzyldiamino diols 2-4, core units of potent C2-symmetric and pseudo-C2-symmetric inhibitors of HIV protease, are described, starting from phenylalanine. Stereoselective epoxidation of trans olefin 7, produced by S(N)2' displacement of an allylic mesylate, followed by regiospecific epoxide opening with lithium azide provided the azido alcohol 8 as the major product. Azide reduction and deprotection led to diamine 1. Protected diamino diols 15-17 were prepared expeditiously by intermolecular titanium- or vanadium-mediated pinacol coupling of protected phenylalaninal. Methods for the stereospecific interconversion of the major (3R,4R,5R,6S) isomer to the desired (3S,4R,5S,6S) isomer via intramolecular hydroxyl inversion are described.

  DOI：

  10.1021/jo00047a023
• 作为产物：
  描述：

  Z-L-苯丙氨醇 在 4-二甲氨基吡啶 、 草酰氯 、 甲烷磺酸 、 TEA 、 水 、 氯化铵 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.75h， 生成 (4S,5R,6S,1'S)-5-acetoxy-4-benzyl-6-<1-<<(benzyloxy)carbonyl>amino>-2-phenylethyl>-3,4,5,6-tetrahydro-2H-1,3-oxazin-2-one
  参考文献：
  名称：

  Stereocontrolled synthesis of C2-symmetric and pseudo-C2-symmetric diamino alcohols and diols for use in HIV protease inhibitors

  摘要：

  The stereocontrolled syntheses of dibenzyldiamino alcohol 1 and dibenzyldiamino diols 2-4, core units of potent C2-symmetric and pseudo-C2-symmetric inhibitors of HIV protease, are described, starting from phenylalanine. Stereoselective epoxidation of trans olefin 7, produced by S(N)2' displacement of an allylic mesylate, followed by regiospecific epoxide opening with lithium azide provided the azido alcohol 8 as the major product. Azide reduction and deprotection led to diamine 1. Protected diamino diols 15-17 were prepared expeditiously by intermolecular titanium- or vanadium-mediated pinacol coupling of protected phenylalaninal. Methods for the stereospecific interconversion of the major (3R,4R,5R,6S) isomer to the desired (3S,4R,5S,6S) isomer via intramolecular hydroxyl inversion are described.

  DOI：

  10.1021/jo00047a023

文献信息

• US5362912A
  申请人：——

  公开号：US5362912A

  公开（公告）日：1994-11-08