Methyl 1,2-O-isopropylidene-5,6-dimethanesulphonyl-α-D-glucofuranoside | 50692-25-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 1,2-O-isopropylidene-5,6-dimethanesulphonyl-α-D-glucofuranoside
• 英文别名: 2,3-O-Isopropylidene-5,6-bis-O-methylsulfonyl-α-D-mannofuranoside；Methyl-2.3-O-isopropyliden-5.6-di-O-methansulfonyl-α-d-mannofuranosid；[(2R)-2-[(3aS,4S,6S,6aS)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]-2-methylsulfonyloxyethyl] methanesulfonate
• CAS: 50692-25-6
• 化学式: C₁₂H₂₂O₁₀S₂
• 分子量: 390.433
• InChiKey: CBEMCDFIYCMBIZ-UVOCVTCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Methyl 1,2-O-isopropylidene-5,6-dimethanesulphonyl-α-D-glucofuranoside 在 铜 、 三乙胺 、 sodium iodide 、 锌 作用下， 以 乙二醇二甲醚 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.17h， 生成 二羧酸乙酯基氧化呋咱
  参考文献：
  名称：

  Blake, Alexander J.; Kirkpatrick, Graeme; McGhie, Karen E., Journal of Carbohydrate Chemistry, 1994, vol. 13, # 3, p. 409 - 420

  摘要：

  DOI：

文献信息

• Some diphenylphosphorus(<scp>V</scp>) group monosaccharide compounds derived from methyl 2,3-O-isopropylidene-α-<scp>D</scp>-mannofuranoside
  作者：Martyn A. Brown、Philip J. Cox、R. Alan Howie、Olga A. Melvin、James L. Wardell

  DOI：10.1039/p19960000809

  日期：——

  Methyl 6-O-diphenylphosphinoyl-2,3-O-isopropylidene-alpha-D-mannofuranoside 2 is obtained by aerial oxidation of the product of the reaction of methyl 2,3-O-isopropylidene-alpha-D-mannofuranoside 1 and Ph(2)PCl in the presence of a base, Methyl 2,3- O-isopropylidene-5,6-bis-O-methylsulfonyl-alpha-D-mannofuranoside 4; R = Me reacts with Ph(2)PLi to give, after aerial oxidation, methyl 6-deoxy-6-C-diphenylphosphinoyl-2,3-O-isopropylidene-5-O-methylsulfonyl-alpha and methyl 6-deoxy-6-C-diphenylphosphinoyl-2,3-O-isopropylidene-beta-L-glufuranoside 6. Also prepared are the 5-O-toluene-p-sulfonyl analogue of compound 2 and 2,3:5,6-bis-O-isopropylidene-1-O-diphenylphosphinoyl-alpha-D-mannofuranoside 8. Crystal structures of compounds 4; (R = Me) and 2 are determined: the furanose ring in both compounds is in a degrees E conformation. Intermolecular H-bonding, involving the P=O and OH groups, links the molecules of compound 2 into chains.