(2R,4S,5R,6S)-5-Acetylamino-4-benzoyloxy-2-bromo-6-((1S,2R)-1,2,3-tris-benzoyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester | 139574-38-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,4S,5R,6S)-5-Acetylamino-4-benzoyloxy-2-bromo-6-((1S,2R)-1,2,3-tris-benzoyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS: 139574-38-2
• 化学式: C₄₀H₃₆BrNO₁₂
• 分子量: 802.629
• InChiKey: JBIUKXXLXZWYPG-GEAXIGPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.08
• 重原子数：
  54.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  169.83
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (2R,4S,5R,6S)-5-Acetylamino-4-benzoyloxy-2-bromo-6-((1S,2R)-1,2,3-tris-benzoyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 在 甲基硫基溴化物 、 3 A molecular sieve 、 silver trifluoromethanesulfonate 、 二异丙胺 作用下， 以 二氯甲烷 、 丙酮 、 乙腈 为溶剂， 反应 6.0h， 生成 (4S,5R,6S)-5-Acetylamino-4-benzoyloxy-6-((1S,2R)-1,2,3-tris-benzoyloxy-propyl)-5,6-dihydro-4H-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  α-selectivity and glycal formation are temperature dependent in glycosylation with sialic acid. Synthesis of a Neu5Acα(2-6)Gal thioglycoside building block

  摘要：

  The glycosylation with the N-acetylneuraminic acid (Neu5Ac) donor 1 of the 6-OH position of D-galactose in various nitriles promoted by methylsulfenyl triflate at different temperatures is reported. The proportion of alpha-sialoside increased and glycal 5 decreased at lower temperatures. A short route to a Neu5Ac-alpha(2-6)Gal thioglycoside building block is also described.

  DOI：

  10.1016/0040-4039(91)80132-p
• 作为产物：
  描述：

  (2R,4S,5R,6S)-5-Acetylamino-2,4-bis-benzoyloxy-6-((1S,2R)-1,2,3-tris-benzoyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 在 氢溴酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (2R,4S,5R,6S)-5-Acetylamino-4-benzoyloxy-2-bromo-6-((1S,2R)-1,2,3-tris-benzoyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
  参考文献：
  名称：

  α-selectivity and glycal formation are temperature dependent in glycosylation with sialic acid. Synthesis of a Neu5Acα(2-6)Gal thioglycoside building block

  摘要：

  The glycosylation with the N-acetylneuraminic acid (Neu5Ac) donor 1 of the 6-OH position of D-galactose in various nitriles promoted by methylsulfenyl triflate at different temperatures is reported. The proportion of alpha-sialoside increased and glycal 5 decreased at lower temperatures. A short route to a Neu5Ac-alpha(2-6)Gal thioglycoside building block is also described.

  DOI：

  10.1016/0040-4039(91)80132-p