4-acetamido-3,7-anhydro-5,6,8-tri-O-benzyl-1,2,4-trideoxy-D-glycero-D-talo-oct-1-ynitol | 443916-45-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-acetamido-3,7-anhydro-5,6,8-tri-O-benzyl-1,2,4-trideoxy-D-glycero-D-talo-oct-1-ynitol
• 英文别名: N-[(2R,3R,4R,5S,6R)-2-ethynyl-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]acetamide
• CAS: 443916-45-8
• 化学式: C₃₁H₃₃NO₅
• 分子量: 499.607
• InChiKey: XJOJLEQHUYADSJ-JQWMYKLHSA-N

物化性质

• 沸点：
  666.6±55.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  37
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-acetamido-3,7-anhydro-5,6,8-tri-O-benzyl-1,2,4-trideoxy-D-glycero-D-talo-oct-1-ynitol 在 4-二甲氨基吡啶 、 sodium acetate 、 对甲苯磺酰肼 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 正己烷 为溶剂， 反应 13.5h， 生成 (R)-4-[3-((2R,3R,4R,5S,6R)-3-Acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-1-(imidazole-1-carbothioyloxy)-propyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
  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 Essentially, these compounds are isosteres of N-glycosyl asparagines in which the amide group has been replaced by an ethylene bridge.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：

  乙酸酐 、 (2R,3R,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-ethynyl-tetrahydro-pyran-3-ylamine 在 吡啶 作用下， 反应 3.0h， 以90%的产率得到4-acetamido-3,7-anhydro-5,6,8-tri-O-benzyl-1,2,4-trideoxy-D-glycero-D-talo-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