3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl chloride | 125411-95-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl chloride
• 英文别名: [(2R,3R,4R,6R)-3,4-diacetyloxy-6-chlorooxan-2-yl]methyl acetate
• CAS: 125411-95-2
• 化学式: C₁₂H₁₇ClO₇
• 分子量: 308.716
• InChiKey: GEGZZOKVBPFVIF-WISYIIOYSA-N

物化性质

• 沸点：
  380.0±42.0 °C(predicted)
• 密度：
  1.29±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  88.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl chloride 、 (3S,8S,9S,10R,13S,14S,17R)-17-[(E,2S,5S)-5-ethyl-6-methylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol 生成 [(2R,3R,4R,6S)-3,4-diacetyloxy-6-[[(3S,8S,9S,10R,13S,14S,17R)-17-[(E,2S,5S)-5-ethyl-6-methylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]oxan-2-yl]methyl acetate
  参考文献：
  名称：

  PETROVIC, JULIJANA;SCANADI, JANOS;CANADI, DERD;PETROVIC, IVANKA;MILJKOVIC+, J. SERB. CHEM. SOC., 54,(1989) N, C. 229-232

  摘要：

  DOI：
• 作为产物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-deoxy-α-D-lyxo-hexopyranose 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl chloride
  参考文献：
  名称：

  Organoboron-Catalyzed Regio- and Stereoselective Formation of β-2-Deoxyglycosidic Linkages

  摘要：

  A borinic acid derived catalyst enables regioselective and β-selective reactions of 2-deoxy- and 2,6-dideoxyglycosyl chloride donors with pyranoside-derived acceptors having unprotected cis-1,2- and 1,3-diol groups. The use of catalysis to promote a β-selective pathway by enhancement of acceptor nucleophilicity constitutes a distinct approach from previous work, which has been aimed at modulating donor reactivity by variation of protective and/or leaving groups.

  DOI：

  10.1021/ol501711v