methyl 3,7-anhydro-5-aza-8-azido-5-(tert-butyl-L-alaninyl)-2,4,5,6,8-pentadeoxy-D-glycero-D-allo-octonate | 813436-17-8

• 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 3,7-anhydro-5-aza-8-azido-5-(tert-butyl-L-alaninyl)-2,4,5,6,8-pentadeoxy-D-glycero-D-allo-octonate
• 英文别名: tert-butyl (2S)-2-[(2S,6S)-2-(azidomethyl)-6-(2-methoxy-2-oxoethyl)morpholin-4-yl]propanoate
• CAS: 813436-17-8
• 化学式: C₁₅H₂₆N₄O₅
• 分子量: 342.395
• InChiKey: WJPSWXMWEJQAPX-SDDRHHMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  79.4
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  methyl 3,7-anhydro-5-aza-8-azido-5-(tert-butyl-L-alaninyl)-2,4,5,6,8-pentadeoxy-D-glycero-D-allo-octonate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 以78%的产率得到3,7-anhydro-5-aza-8-azido-5-(tert-butyl-L-alaninyl)-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 、 sodium cyanoborohydride 、 溶剂黄146 、 高碘酸 、 原甲酸三甲酯 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 32.33h， 生成 methyl 3,7-anhydro-5-aza-8-azido-5-(tert-butyl-L-alaninyl)-2,4,5,6,8-pentadeoxy-D-glycero-D-allo-octonate
  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

文献信息

• Synthesis and Application of Carbohydrate-Derived Morpholine Amino Acids
  作者：Gijsbert M. Grotenbreg、Alphert E. Christina、Annelies E. M. Buizert、Gijsbert A. van der Marel、Herman S. Overkleeft、Mark Overhand

  DOI：10.1021/jo048630x

  日期：2004.11.1

  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.