3,7-anhydro-4-azido-5,6,8-tri-O-benzyl-1,2,4-trideoxy-D-glycero-D-galacto-oct-1-ynitol | 443916-31-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,7-anhydro-4-azido-5,6,8-tri-O-benzyl-1,2,4-trideoxy-D-glycero-D-galacto-oct-1-ynitol
• 英文别名: (2S,3R,4R,5S,6R)-3-azido-2-ethynyl-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxane
• CAS: 443916-31-2
• 化学式: C₂₉H₂₉N₃O₄
• 分子量: 483.567
• InChiKey: STXAICNJDJYDKW-MMBNBZRISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  36
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  51.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  三苯基膦 、 3,7-anhydro-4-azido-5,6,8-tri-O-benzyl-1,2,4-trideoxy-D-glycero-D-galacto-oct-1-ynitol 以 四氢呋喃 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Synthesis of α- and β-Glycosyl Asparagine Ethylene Isosteres (C-Glycosyl Asparagines) via Sugar Acetylenes and Garner Aldehyde Coupling

  摘要：

  A convergent approach has been developed for the synthesis of C-glycosyl amino acids in which the glycinyl moiety CH(NH2)CO2H is connected to the anomeric center of the sugar residue by a three carbon atom tether. Essentially, these compounds are isosteres of N-glycosyl asparagines in which the amide group has been replaced by an ethylene bridge. Following the coupling of alpha- or beta-D-linked lithium C-glycoside acetylides with N-Boc D-serinal acetonide (Garner aldehyde), the resulting adducts were transformed into the final N-Boc-C-glycosyl-alpha-aminopentanoic acids via reduction of the triple bond, deoxygenation, and oxidative cleavage of the oxazolidine ring. By this protocol, 12 C-glycosyl asparagines, six pairs of alpha- and beta-anomers, have been prepared incorporating the gluco, galacto, manno, and the corresponding 2-acetamido-2-deoxy residues.

  DOI：

  10.1021/jo020054m
• 作为产物：
  描述：

  ((3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylethynyl)-trimethyl-silane 在 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 以94%的产率得到3,7-anhydro-4-azido-5,6,8-tri-O-benzyl-1,2,4-trideoxy-D-glycero-D-galacto-oct-1-ynitol
  参考文献：
  名称：

  Synthesis of α- and β-Glycosyl Asparagine Ethylene Isosteres (C-Glycosyl Asparagines) via Sugar Acetylenes and Garner Aldehyde Coupling

  摘要：

  A convergent approach has been developed for the synthesis of C-glycosyl amino acids in which the glycinyl moiety CH(NH2)CO2H is connected to the anomeric center of the sugar residue by a three carbon atom tether. Essentially, these compounds are isosteres of N-glycosyl asparagines in which the amide group has been replaced by an ethylene bridge. Following the coupling of alpha- or beta-D-linked lithium C-glycoside acetylides with N-Boc D-serinal acetonide (Garner aldehyde), the resulting adducts were transformed into the final N-Boc-C-glycosyl-alpha-aminopentanoic acids via reduction of the triple bond, deoxygenation, and oxidative cleavage of the oxazolidine ring. By this protocol, 12 C-glycosyl asparagines, six pairs of alpha- and beta-anomers, have been prepared incorporating the gluco, galacto, manno, and the corresponding 2-acetamido-2-deoxy residues.

  DOI：

  10.1021/jo020054m