methyl 4-O-β-D-galactopyranosyl-α-D-mannopyranoside | 92282-08-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 4-O-β-D-galactopyranosyl-α-D-mannopyranoside
• 英文别名: methyl-(O⁴-β-D-galactopyranosyl-α-D-mannopyranoside)；Methyl-(O⁴-β-D-galactopyranosyl-α-D-mannopyranosid)；4-O-β-D-Galactopyranosyl-methyl-α-D-mannopyranosid；Methyl 4-O-beta-D-galactopyranosyl-alpha-D-mannopyranoside；(2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5S,6S)-4,5-dihydroxy-2-(hydroxymethyl)-6-methoxyoxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 92282-08-1
• 化学式: C₁₃H₂₄O₁₁
• 分子量: 356.327
• InChiKey: FHNIYFZSHCGBPP-IYQPGZRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.2
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  179
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 methyl 4-O-β-D-galactopyranosyl-α-D-mannopyranoside 在 sodium acetate 作用下， 生成 methyl-[O2,O3,O6-triacetyl-O4-(tetra-O-acetyl-β-D-galactopyranosyl)-β-D-altropyranoside]
  参考文献：
  名称：

  Haworth et al., Journal of the Chemical Society, 1930, p. 2636,2638

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl-[O2,O3,O6-triacetyl-O4-(tetra-O-acetyl-β-D-galactopyranosyl)-β-D-altropyranoside] 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以5.5 mg的产率得到methyl 4-O-β-D-galactopyranosyl-α-D-mannopyranoside
  参考文献：
  名称：

  Glycosidic Torsional Motions in a Bicelle-associated Disaccharide from Residual Dipolar Couplings

  摘要：

  An analysis of torsional motions about glycosidic bonds in a disaccharide is undertaken using residual dipolar coupling measurements and selective immobilization of the reducing end sugar to provide a suitable motional reference. The immobilization is accomplished by using the short chain of an alkyl glycoside to anchor the disaccharide to a bilayer medium aligned in magnetic field. Motions about the beta-(1-4) linkage of the n-butyl-4-O-beta-d-galactopyranosyl-alpha-d-mannopyranoside are shown to be substantial (+/-40 degrees ) and in good agreement with predictions of a fully solvated molecular dynamics simulation.

  DOI：

  10.1021/ja045697t

文献信息

• Haworth et al., Journal of the Chemical Society, <hi>1931</hi>, p. 1349,1351
  作者：Haworth et al.

  DOI：——

  日期：——
• Haworth et al., Journal of the Chemical Society, 1930, p. 2636,2638
  作者：Haworth et al.

  DOI：——

  日期：——
• Glycosidic Torsional Motions in a Bicelle-associated Disaccharide from Residual Dipolar Couplings
  作者：Xiaobing Yi、André Venot、John Glushka、James H. Prestegard

  DOI：10.1021/ja045697t

  日期：2004.10.1

  An analysis of torsional motions about glycosidic bonds in a disaccharide is undertaken using residual dipolar coupling measurements and selective immobilization of the reducing end sugar to provide a suitable motional reference. The immobilization is accomplished by using the short chain of an alkyl glycoside to anchor the disaccharide to a bilayer medium aligned in magnetic field. Motions about the beta-(1-4) linkage of the n-butyl-4-O-beta-d-galactopyranosyl-alpha-d-mannopyranoside are shown to be substantial (+/-40 degrees ) and in good agreement with predictions of a fully solvated molecular dynamics simulation.