4-acetamido-3,7-anhydro-5,6,8-tri-O-benzyl-1,2,4-trideoxy-D-glycero-D-gulo-oct-1-ynitol | 443916-42-5

• 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-gulo-oct-1-ynitol
• 英文别名: N-[(2S,3S,4R,5S,6R)-2-ethynyl-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl]acetamide
• CAS: 443916-42-5
• 化学式: C₃₁H₃₃NO₅
• 分子量: 499.607
• InChiKey: XJOJLEQHUYADSJ-JWXZHISWSA-N

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-gulo-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-((2S,3S,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 Essentially, these compounds are isosteres of N-glycosyl asparagines in which the amide group has been replaced by an ethylene bridge.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：

  N-[(2S,3S,4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((E)-propenyl)-tetrahydro-pyran-3-yl]-acetamide 在 sodium periodate 、 四氧化锇 、 甲醇 、 (1-重氮基-2-氧代丙基)膦酸二甲酯 、 potassium carbonate 作用下， 以 四氢呋喃 、 水 为溶剂， 以52%的产率得到4-acetamido-3,7-anhydro-5,6,8-tri-O-benzyl-1,2,4-trideoxy-D-glycero-D-gulo-oct-1-ynitol
  参考文献：
  名称：

  Synthesis of α- and β-C-glycosides of N-acetylglucosamine

  摘要：

  As part of efforts to make available new, classes of bioactive C-glycoconjugates, D-glucosamine has been effectively converted into a series of 2-deoxy-2-amino-C-glycosides. This versatile approach is keyed by a remarkably effective metal catalyzed olefin isomerization of the isomeric C-allyl amino sugars which, in turn, are readily available via radical allylation of D-glucosamine. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)00818-9