methyl 2,4,6-tri-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-α-D-galactopyranoside | 950677-76-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,4,6-tri-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-α-D-galactopyranoside
• CAS: 950677-76-6
• 化学式: C₂₇H₃₈O₁₈
• 分子量: 650.588
• InChiKey: UHSQXNOZAXQAJT-YMRDTZBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.75
• 重原子数：
  45.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  221.02
• 氢给体数：
  0.0
• 氢受体数：
  18.0

反应信息

• 作为反应物：
  描述：

  methyl 2,4,6-tri-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-α-D-galactopyranoside 在 硫酸 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 10.0h， 生成 3-O-(α-D-glucopyranosyl)-D-galactopyranose
  参考文献：
  名称：

  The synthesis of 2-, 3-, 4- and 6-O-α-d-glucopyranosyl-d-galactopyranose, and their evaluation as nutritional supplements for pre-term infants

  摘要：

  Four methods have been screened for the synthesis of some alpha-D-glucopyrano sides, with the recently reported (Mukaiyama) combination of 2,3,4,6-tetra-O-benzyl- alpha-D-glucopyranosyl iodide and triphenylphosphine oxide being the most successful, especially in the diastereoselectivity exhibited. The alpha-D-glueopyranosides so obtained have been deprotected to yield 2-, 3-, 4- and 6-O-alpha-D-glucopyranosyl-D-galactopyranose. Only the last disaccharide showed any hydrolysis by alpha-glycosidases but this success was not emulated by mucosal extracts from the small intestine of the pig. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.04.022
• 作为产物：
  描述：

  、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 8.0h， 以64%的产率得到methyl 2,4,6-tri-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-α-D-galactopyranoside
  参考文献：
  名称：

  The synthesis of 2-, 3-, 4- and 6-O-α-d-glucopyranosyl-d-galactopyranose, and their evaluation as nutritional supplements for pre-term infants

  摘要：

  Four methods have been screened for the synthesis of some alpha-D-glucopyrano sides, with the recently reported (Mukaiyama) combination of 2,3,4,6-tetra-O-benzyl- alpha-D-glucopyranosyl iodide and triphenylphosphine oxide being the most successful, especially in the diastereoselectivity exhibited. The alpha-D-glueopyranosides so obtained have been deprotected to yield 2-, 3-, 4- and 6-O-alpha-D-glucopyranosyl-D-galactopyranose. Only the last disaccharide showed any hydrolysis by alpha-glycosidases but this success was not emulated by mucosal extracts from the small intestine of the pig. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2007.04.022