(3S,4S)-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexyl-2-(diethoxymethyl)-3-hydroxy-1-pentene | 120476-96-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,4S)-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexyl-2-(diethoxymethyl)-3-hydroxy-1-pentene
• 英文别名: (3S,4S)-4-[(tert-butyloxycarbonyl)amino]-5-cyclohexyl-2-(diethoxymethyl)-3-hydroxy-1-pentene；tert-butyl N-[(2S,3S)-1-cyclohexyl-4-(diethoxymethyl)-3-hydroxypent-4-en-2-yl]carbamate
• CAS: 120476-96-2
• 化学式: C₂₁H₃₉NO₅
• 分子量: 385.544
• InChiKey: KDERAMALZRTRJB-ROUUACIJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.17
• 重原子数：
  27.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  77.02
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (3S,4S)-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexyl-2-(diethoxymethyl)-3-hydroxy-1-pentene 在 sodium tetrahydroborate 、 草酸 、 sodium hydride 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (4S,5S)-4-(cyclohexylmethyl)-5-(3'-hydroxy-2'-propenyl)oxazolidin-2-one
  参考文献：
  名称：

  Azido glycols: potent, low molecular weight renin inhibitors containing an unusual post scissile site residue

  摘要：

  Azidomethyl-substituted 1,2- and 1,3-diols were prepared from Boc-cyclohexylalanal and evaluated as transition state analogue renin inhibitors, leading to the development of a small (MW less than 600), nanomolar inhibitor. Remarkable aqueous solubility enhancement followed the incorporation of an N-terminal urea functionality. Evaluation of selected compounds both in vivo and in vitro demonstrated that while transport across the intestine occurred upon id administration, extensive liver extraction resulted in low systemic levels.

  DOI：

  10.1021/jm00126a038
• 作为产物：
  描述：

  2-溴丙烯醛二乙缩醛 、 2-甲基-2-丙基[(2S)-1-环己基-3-氧代-2-丙基]氨基甲酸酯 在 正丁基锂 作用下， 生成 (3R,4S)-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexyl-2-(diethoxymethyl)-3-hydroxy-1-pentene 、 (3S,4S)-4-<(tert-butyloxycarbonyl)amino>-5-cyclohexyl-2-(diethoxymethyl)-3-hydroxy-1-pentene
  参考文献：
  名称：

  Azido glycols: potent, low molecular weight renin inhibitors containing an unusual post scissile site residue

  摘要：

  Azidomethyl-substituted 1,2- and 1,3-diols were prepared from Boc-cyclohexylalanal and evaluated as transition state analogue renin inhibitors, leading to the development of a small (MW less than 600), nanomolar inhibitor. Remarkable aqueous solubility enhancement followed the incorporation of an N-terminal urea functionality. Evaluation of selected compounds both in vivo and in vitro demonstrated that while transport across the intestine occurred upon id administration, extensive liver extraction resulted in low systemic levels.

  DOI：

  10.1021/jm00126a038

文献信息

• ROSENBERG, SAUL H.;WOODS, KEITH W.;KLEINERT, HOLLIS D.;STEIN, HERMAN;NELL+, J. MED. CHEM., 32,(1989) N, C. 1371-1378
  作者：ROSENBERG, SAUL H.、WOODS, KEITH W.、KLEINERT, HOLLIS D.、STEIN, HERMAN、NELL+

  DOI：——

  日期：——