methyl [3S,4R,6S,9R]-1-aza-3-[2,2,2-trifluoroacetylamino]-4-carbobenzyloxy-2-oxo-7-thiabicyclic[4.3.0]-nonane-9-carboxylate

• 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: methyl [3S,4R,6S,9R]-1-aza-3-[2,2,2-trifluoroacetylamino]-4-carbobenzyloxy-2-oxo-7-thiabicyclic[4.3.0]-nonane-9-carboxylate
• 英文别名: 7-O-benzyl 3-O-methyl (3R,6S,7S,8aR)-5-oxo-6-[(2,2,2-trifluoroacetyl)amino]-2,3,6,7,8,8a-hexahydro-[1,3]thiazolo[3,2-a]pyridine-3,7-dicarboxylate
• 化学式: C₁₉H₁₉F₃N₂O₆S
• 分子量: 460.431
• InChiKey: FBSWELHLMGFRQT-FQUUOJAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  127
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  4-benzyl 1-methyl N-(tert-butoxycarbonyl)-L-aspartate 在 六甲基磷酰三胺 、 sodium periodate 、 四氧化锇 、 molecular sieve 、 4 A molecular sieve 、 三氟乙酸 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 吡啶 、 二氯甲烷 、 水 为溶剂， 反应 80.5h， 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
  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.