methyl(5-acetamido-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranose) | 20298-35-5

• 物质功能分类: 生物化工 - 糖类化合物 - 单糖
• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl(5-acetamido-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranose)
• 英文别名: methyl (2S,4S,5R,6S)-5-acetamido-2,4-dihydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylate
• CAS: 20298-35-5；22900-11-4；100678-43-1；109121-98-4；109122-00-1；119241-60-0；119241-61-1；119241-62-2
• 化学式: C₁₂H₂₁NO₉
• 分子量: 323.3
• InChiKey: BKZQMWNJESHHSA-XKVSGUBFSA-N

物化性质

• 熔点：
  193.5-194.5°C
• 沸点：
  693.8±55.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)
• 溶解度：
  溶于甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  -3.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  166
• 氢给体数：
  6
• 氢受体数：
  9

制备方法与用途

用途

N-乙酰神经氨酸甲酯是羧酸酯类的有机化合物，可用作生物化学试剂。

反应信息

• 作为反应物：
  描述：

  苯甲酰氯 、 methyl(5-acetamido-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranose) 在 吡啶 作用下， 反应 24.0h， 以11%的产率得到(2S,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
  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

文献信息

• α-selectivity and glycal formation are temperature dependent in glycosylation with sialic acid. Synthesis of a Neu5Acα(2-6)Gal thioglycoside building block
  作者：Winnie Birberg、Hans Lönn

  DOI：10.1016/0040-4039(91)80132-p

  日期：1991.12

  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.