4-(1,3-dioxolan-2-yl)-3-oxabutyl 2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside | 219838-60-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 4-(1,3-dioxolan-2-yl)-3-oxabutyl 2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside
• CAS: 219838-60-5
• 化学式: C₂₁H₂₉N₃O₈
• 分子量: 451.477
• InChiKey: WOOMIQYGEUTVNW-ATUYUNQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.33
• 重原子数：
  32.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  130.44
• 氢给体数：
  0.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  4-(1,3-dioxolan-2-yl)-3-oxabutyl 2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside 在 palladium on activated charcoal 吡啶 、 molecular sieve 、 三氟甲磺酸三甲基硅酯 、 氢气 、 sodium methylate 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 29.25h， 生成 4-(1,3-dioxolan-2-yl)-3-oxabutyl 2-O-<2,3-di-O-acetyl-4-(2,4-di-O-acetyl-3-deoxy-L-glycero-tetronyl)-4,6-dideoxy-α-D-mannopyranosyl>-4-(2,4-di-O-acetyl-3-deoxy-L-glycero-tetronyl)-3-O-acetyl-4,6-dideoxy-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of theVibrio CholeraeO1 Ogawa and Inaba Terminal Disaccharides With Dioxolane-Type Spacers and their Coupling to Proteins¹

  摘要：

  The disaccharide, which corresponds to the terminal fragment of the Vibrio cholerae O1 LPS, was prepared starting from the corresponding trichloroacetimidate derivative of the monosaccharide in the presence of trimethylsilyl triflate. After selective reduction of the azido group, the reaction with 2,4-di-O-acetyl-3-deoxy-L-glycero-tetronic acid in the presence of EEDQ afforded the corresponding amides. The cleavage of dioxolane protecting group followed by careful deacetylation and coupling with Bovine Serum Albumin or Meningococcal Outer Membrane Protein in the presence of sodium cyanoborohydride gave the corresponding neoglycoconjugates.

  DOI：

  10.1080/07328309808002355
• 作为产物：
  描述：

  Acetic acid (2S,3S,4S,5R,6R)-5-azido-4-benzyloxy-2-hydroxy-6-methyl-tetrahydro-pyran-3-yl ester 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 24.25h， 生成 4-(1,3-dioxolan-2-yl)-3-oxabutyl 2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of theVibrio CholeraeO1 Ogawa and Inaba Terminal Disaccharides With Dioxolane-Type Spacers and their Coupling to Proteins¹

  摘要：

  The disaccharide, which corresponds to the terminal fragment of the Vibrio cholerae O1 LPS, was prepared starting from the corresponding trichloroacetimidate derivative of the monosaccharide in the presence of trimethylsilyl triflate. After selective reduction of the azido group, the reaction with 2,4-di-O-acetyl-3-deoxy-L-glycero-tetronic acid in the presence of EEDQ afforded the corresponding amides. The cleavage of dioxolane protecting group followed by careful deacetylation and coupling with Bovine Serum Albumin or Meningococcal Outer Membrane Protein in the presence of sodium cyanoborohydride gave the corresponding neoglycoconjugates.

  DOI：

  10.1080/07328309808002355