{(S)-1-[(1S,2R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanylsulfanylmethyl)-propylcarbamoyl]-3-carbamoyl-propyl}-carbamic acid tert-butyl ester | 870196-24-0

• 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: {(S)-1-[(1S,2R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanylsulfanylmethyl)-propylcarbamoyl]-3-carbamoyl-propyl}-carbamic acid tert-butyl ester
• CAS: 870196-24-0
• 化学式: C₄₆H₆₃N₃O₅SSi₂
• 分子量: 826.26
• InChiKey: SXUNJHAJLHUJLX-ZSVDBMLLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.89
• 重原子数：
  57.0
• 可旋转键数：
  16.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  119.75
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  {(S)-1-[(1S,2R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanylsulfanylmethyl)-propylcarbamoyl]-3-carbamoyl-propyl}-carbamic acid tert-butyl ester 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 0.5h， 以73%的产率得到(S)-2-Amino-pentanedioic acid 5-amide 1-{[(1S,2R)-2-(tert-butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanylsulfanylmethyl)-propyl]-amide}
  参考文献：
  名称：

  Synthesis of (2R,3S) 3-amino-4-mercapto-2-butanol, a threonine analogue for covalent inhibition of sortases

  摘要：

  L-Threonine 2 was converted in seven steps into the protected aminomercaptoalcohol 8, a threonine mimic. This compound 8 was coupled to various oligopeptides to produce two different tetrapeptide analogues, for example, 11 and 17, which were shown to inhibit the Sortase enzymes (SrtA and SrtB) via covalent attachment of the thiol groups of 11 and 17 to the catalytically active cysteine residue of the Sortase enzymes. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.073
• 作为产物：
  描述：

  [(1R,2R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-hydroxymethyl-propyl]-carbamic acid tert-butyl ester 在 盐酸 、 四溴化碳 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 三乙胺 、 N,N-二异丙基乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 55.33h， 生成 {(S)-1-[(1S,2R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-(tert-butyl-diphenyl-silanylsulfanylmethyl)-propylcarbamoyl]-3-carbamoyl-propyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Synthesis of (2R,3S) 3-amino-4-mercapto-2-butanol, a threonine analogue for covalent inhibition of sortases

  摘要：

  L-Threonine 2 was converted in seven steps into the protected aminomercaptoalcohol 8, a threonine mimic. This compound 8 was coupled to various oligopeptides to produce two different tetrapeptide analogues, for example, 11 and 17, which were shown to inhibit the Sortase enzymes (SrtA and SrtB) via covalent attachment of the thiol groups of 11 and 17 to the catalytically active cysteine residue of the Sortase enzymes. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.07.073