(S)-3-((R)-2-Azido-1-formyl-ethoxy)-4-oxo-butyric acid methyl ester | 851885-53-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (S)-3-((R)-2-Azido-1-formyl-ethoxy)-4-oxo-butyric acid methyl ester
• CAS: 851885-53-5
• 化学式: C₈H₁₁N₃O₅
• 分子量: 229.192
• InChiKey: VHYARAVAYQHCNS-NKWVEPMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.01
• 重原子数：
  16.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  118.43
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S)-3-((R)-2-Azido-1-formyl-ethoxy)-4-oxo-butyric acid methyl ester 在 sodium hydroxide 、 sodium cyanoborohydride 、 溶剂黄146 、 原甲酸三甲酯 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 20.0h， 生成 3,7-anhydro-5-aza-8-azido-5-p-methoxybenzyl-2,4,5,6,8-pentadeoxy-D-glycero-D-allo-octonic acid
  参考文献：
  名称：

  Synthesis and Application of Carbohydrate-Derived Morpholine Amino Acids

  摘要：

  The synthesis of series of diversely functionalized epsilon-morpholine amino acids (MAAs, 5a-h) starting from an E-sugar amino acid and following a two-step oxidative glycol cleavage/reductive amination strategy, is described. In an alternative synthetic scheme, diastereoisomerically pure delta-MAAs (12a,b) were obtained. Oligopeptides containing MAAs were prepared either by direct incorporation of a MAA building block or by subjecting a fully assembled SAA-containing peptide to the two-step glycol cleavage/reductive amination procedure.

  DOI：

  10.1021/jo048630x
• 作为产物：
  描述：

  methyl 3,6-anhydro-7-azido-2,7-dideoxy-4,5-O-isopropylidene-D-allo-heptulonate 在 盐酸 、 高碘酸 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 16.33h， 生成 (S)-3-((R)-2-Azido-1-formyl-ethoxy)-4-oxo-butyric acid methyl ester
  参考文献：
  名称：

  Synthesis and Application of Carbohydrate-Derived Morpholine Amino Acids

  摘要：

  The synthesis of series of diversely functionalized epsilon-morpholine amino acids (MAAs, 5a-h) starting from an E-sugar amino acid and following a two-step oxidative glycol cleavage/reductive amination strategy, is described. In an alternative synthetic scheme, diastereoisomerically pure delta-MAAs (12a,b) were obtained. Oligopeptides containing MAAs were prepared either by direct incorporation of a MAA building block or by subjecting a fully assembled SAA-containing peptide to the two-step glycol cleavage/reductive amination procedure.

  DOI：

  10.1021/jo048630x