(6S)-<6-2H>Methyl -(2-6)-β-D-galactopyranoside | 131904-52-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (6S)-<6-2H>Methyl -(2-6)-β-D-galactopyranoside
• 英文别名: (6S)-[6-2H]Methyl [methyl (5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl)onate]-(2-6)-β-D-galactopyranoside
• CAS: 131904-52-4；132015-20-4；132071-93-3
• 化学式: C₁₉H₃₃NO₁₄
• 分子量: 500.461
• InChiKey: SOAAWTGOCXHFQN-DNEWKNBCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.31
• 重原子数：
  34.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  233.93
• 氢给体数：
  8.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  (6S)-<6-2H>Methyl -(2-6)-β-D-galactopyranoside 在 sodium hydroxide 作用下， 反应 0.5h， 以55%的产率得到(6S)-<6-2H>Methyl <(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosyl)onic>-(2-6)-β-D-galactopyranoside
  参考文献：
  名称：

  Preferred conformation about the C5-C6 bond of N-acetylneuraminyl(2-6)-D-galacto- and -D-glucopyranosides in solution

  摘要：

  Diastereoselective deuteration and H-1 NMR spectroscopy were applied in a conformational study of the C5-C6 bond in four stereoisomeric methyl N-acetylneuraminyl(2-6)-beta-D-hexopyranosides [NeuNAc-alpha(2-6)Gal, NeuNAc-beta-(2-6)Gal, NeuNAc-alpha-(2-6)Glc, and NeuNAc-beta-(2-6)Glc]. In aqueous solution, NeuNAc-alpha-(2-6)Gal prefers a gt conformer (gg:gt:tg = ca. 20:60:20), NeuNAc(2-6)Glc isomers prefer a gg (gg:gt:tg = ca. 60:40:0), and NeuNAc-beta-(2-6)Gal exists equally in the three conformers.

  DOI：

  10.1021/jo00005a015
• 作为产物：
  描述：

  N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester 在 钯 4 A molecular sieve 、 氢气 、 氰化汞 、 mercury dibromide 作用下， 以 甲醇 、 二氯甲烷 、 溶剂黄146 为溶剂， 反应 30.0h， 生成 (6S)-<6-2H>Methyl -(2-6)-β-D-galactopyranoside
  参考文献：
  名称：

  Preferred conformation about the C5-C6 bond of N-acetylneuraminyl(2-6)-D-galacto- and -D-glucopyranosides in solution

  摘要：

  Diastereoselective deuteration and H-1 NMR spectroscopy were applied in a conformational study of the C5-C6 bond in four stereoisomeric methyl N-acetylneuraminyl(2-6)-beta-D-hexopyranosides [NeuNAc-alpha(2-6)Gal, NeuNAc-beta-(2-6)Gal, NeuNAc-alpha-(2-6)Glc, and NeuNAc-beta-(2-6)Glc]. In aqueous solution, NeuNAc-alpha-(2-6)Gal prefers a gt conformer (gg:gt:tg = ca. 20:60:20), NeuNAc(2-6)Glc isomers prefer a gg (gg:gt:tg = ca. 60:40:0), and NeuNAc-beta-(2-6)Gal exists equally in the three conformers.

  DOI：

  10.1021/jo00005a015