4-O-benzyl 1-O-methyl (2S,3R)-3-(2-oxoethyl)-2-[(2,2,2-trifluoroacetyl)amino]butanedioate | 700816-02-0

• 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: 4-O-benzyl 1-O-methyl (2S,3R)-3-(2-oxoethyl)-2-[(2,2,2-trifluoroacetyl)amino]butanedioate
• CAS: 700816-02-0
• 化学式: C₁₆H₁₆F₃NO₆
• 分子量: 375.301
• InChiKey: QNBWTBQFCILZIE-NEPJUHHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  98.8
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 L-半胱氨酸 、 4-O-benzyl 1-O-methyl (2S,3R)-3-(2-oxoethyl)-2-[(2,2,2-trifluoroacetyl)amino]butanedioate 以 吡啶 为溶剂， 反应 76.0h， 生成 methyl [3S,4R,6S,9R]-1-aza-3-[2,2,2-trifluoroacetylamino]-4-carbobenzyloxy-2-oxo-7-thiabicyclic[4.3.0]-nonane-9-carboxylate 、 methyl [3S,4R,6S.9R]-1-aza-3-[2,2,2-trifluoroacetylamino]-4-carbobenzyloxy-2-oxo-7-thiabicyclic[4.3.0]-nonane-9-carboxylate
  参考文献：
  名称：

  A simple and efficient synthesis of an Asp-Gly dipeptide mimetic

  摘要：

  Alkylation of N-alpha-Boc protected aspartic acid with allyl bromide in the presence of lithium bis(trimethylsilyl)amide (LHMDS) and hexamethylphosphoramide (HMPA) afforded chiral P-allyl substituted aspartic acid in good yields. After deprotection of the N-alpha-Boc group and reprotection as a trifluoroacetamide, the terminal alkene was oxidized to an aldehyde. The aldehyde was then coupled with L-cysteine through a cascade three-bond formation process to afford aspartic acid-glycine bicyclic dipeptide mimetics. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.02.117
• 作为产物：
  描述：

  methyl 2-(2,2,2-trifluoro-acetylamino)-3-carbobenzyloxy-(2S,3R)-hex-5-enoate 在 四氧化锇 、 sodium periodate 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.08h， 生成 4-O-benzyl 1-O-methyl (2S,3R)-3-(2-oxoethyl)-2-[(2,2,2-trifluoroacetyl)amino]butanedioate
  参考文献：
  名称：

  A simple and efficient synthesis of an Asp-Gly dipeptide mimetic

  摘要：

  Alkylation of N-alpha-Boc protected aspartic acid with allyl bromide in the presence of lithium bis(trimethylsilyl)amide (LHMDS) and hexamethylphosphoramide (HMPA) afforded chiral P-allyl substituted aspartic acid in good yields. After deprotection of the N-alpha-Boc group and reprotection as a trifluoroacetamide, the terminal alkene was oxidized to an aldehyde. The aldehyde was then coupled with L-cysteine through a cascade three-bond formation process to afford aspartic acid-glycine bicyclic dipeptide mimetics. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2004.02.117

文献信息

• A simple and efficient synthesis of an Asp-Gly dipeptide mimetic
  作者：John M. Ndungu、Xuyuan Gu、Dustin E. Gross、Jinfa Ying、Victor J. Hruby

  DOI：10.1016/j.tetlet.2004.02.117

  日期：2004.4

  Alkylation of N-alpha-Boc protected aspartic acid with allyl bromide in the presence of lithium bis(trimethylsilyl)amide (LHMDS) and hexamethylphosphoramide (HMPA) afforded chiral P-allyl substituted aspartic acid in good yields. After deprotection of the N-alpha-Boc group and reprotection as a trifluoroacetamide, the terminal alkene was oxidized to an aldehyde. The aldehyde was then coupled with L-cysteine through a cascade three-bond formation process to afford aspartic acid-glycine bicyclic dipeptide mimetics. (C) 2004 Elsevier Ltd. All rights reserved.