methyl 2,3-di-O-benzyl-4-deoxy-4-fluoro-β-D-galactopyranoside | 51996-35-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl 2,3-di-O-benzyl-4-deoxy-4-fluoro-β-D-galactopyranoside
• 英文别名: [(2R,3S,4R,5R,6R)-3-fluoro-6-methoxy-4,5-bis(phenylmethoxy)oxan-2-yl]methanol
• CAS: 51996-35-1
• 化学式: C₂₁H₂₅FO₅
• 分子量: 376.425
• InChiKey: DWZIZFSOGSMHDV-XDWAVFMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-O-benzyl-4-deoxy-4-fluoro-β-D-galactopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 14.0h， 生成 甲基 4-脱氧-4-氟-D-吡喃半乳糖苷
  参考文献：
  名称：

  Specificity of α- and β-d-galactosidase towards analogs of d-galactopyranosides modified at C-4 or C-5

  摘要：

  DOI：

  10.1016/s0008-6215(00)85562-7
• 作为产物：
  描述：

  methyl 2,3-di-O-benzyl-β-D-glucopyranoside 在 吡啶 、 Amberlite A-26-F (3.5 meq. of F(-)/g) 、 sodium methylate 作用下， 以 甲醇 、 苯 为溶剂， 生成 methyl 2,3-di-O-benzyl-4-deoxy-4-fluoro-β-D-galactopyranoside
  参考文献：
  名称：

  Preparation of two methyl deoxyfluoro-β-d-galactopyranosides, and their interaction with galactan-specific immunoglobulin A 1539 (fab′)

  摘要：

  Methyl 2-deoxy-2-fluoro-beta-D-glactopyranoside (2) and methyl 4-deoxy-4-fluoro-beta-D-glactopyranoside (7) have been prepared, and the possibility of their binding to (1 leads to 6)-beta-D-galactopyranan-specific immunoglobulin A J539 (Fab') has been investigated. Compound 2 does not show binding, whereas 7 does. It appears that the 2-hydroxyl group of methyl beta-D-galactopyranoside may take part in hydrogen bonding to the protein.

  DOI：

  10.1016/s0008-6215(00)85575-5

文献信息

• Specificity of α- and β-d-galactosidase towards analogs of d-galactopyranosides modified at C-4 or C-5
  作者：Jeong E. Nam Shin、Asafu Maradufu、Jean Marion、Arthur S. Perlin

  DOI：10.1016/s0008-6215(00)85562-7

  日期：1980.9
• Preparation of two methyl deoxyfluoro-β-d-galactopyranosides, and their interaction with galactan-specific immunoglobulin A 1539 (fab′)
  作者：Yitzhak Ittah、Cornelis P.J. Glaudemans

  DOI：10.1016/s0008-6215(00)85575-5

  日期：1981.9

  Methyl 2-deoxy-2-fluoro-beta-D-glactopyranoside (2) and methyl 4-deoxy-4-fluoro-beta-D-glactopyranoside (7) have been prepared, and the possibility of their binding to (1 leads to 6)-beta-D-galactopyranan-specific immunoglobulin A J539 (Fab') has been investigated. Compound 2 does not show binding, whereas 7 does. It appears that the 2-hydroxyl group of methyl beta-D-galactopyranoside may take part in hydrogen bonding to the protein.