1,4:3,6-dianhydro-β-D-fructofuranosyl 4-chloro-4-deoxy-α-D-galactopyranoside | 813413-37-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 呋喃类
• 英文名称: 1,4:3,6-dianhydro-β-D-fructofuranosyl 4-chloro-4-deoxy-α-D-galactopyranoside
• 英文别名: (2R,3R,4R,5R,6R)-5-chloro-6-(hydroxymethyl)-2-[[(1S,3R,6S,7R)-2,5,8-trioxatricyclo[4.3.0.03,7]nonan-1-yl]oxy]oxane-3,4-diol
• CAS: 813413-37-5
• 化学式: C₁₂H₁₇ClO₈
• 分子量: 324.715
• InChiKey: ZJRPHOGCBPEUOR-QZUDCSBFSA-N

物化性质

• 熔点：
  90-92 °C
• 沸点：
  562.6±50.0 °C(Predicted)
• 密度：
  1.69±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  107
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,4:3,6-dianhydro-β-D-fructofuranosyl 4-chloro-4-deoxy-α-D-galactopyranoside 在 硫酸 作用下， 以 水 为溶剂， 反应 2.0h， 以91%的产率得到4-氯-4-脱氧-Α-D-吡喃半乳糖
  参考文献：
  名称：

  Preparation of α and β anomers of 1,2,3,6-tetra-O-acetyl-4-chloro-4-deoxy-d-galactopyranose based upon anomerization and kinetic acetylation

  摘要：

  4-Chloro-4-deOXY-alpha-D-galactopyranose, 1,2,3,6-tetra-O-acetyl-4-chloro-4-deoxy-alpha-D-galactopyranose and 1,2,3,6-tetra-O-acetyl-4-chloro-4-deoxy-beta-D-galactopyranose were readily prepared from 1,4:3,6-dianhydro-beta-D-fructofuranosyl 4-chloro-4-deoxy-alpha- D-galactopyranoside. In the study, we found an interesting anomerization phenomenon of 4-chloro-4-deoxy-D-galactose. The molar ratio of alpha and beta anomers in solution is about 1:2 when the anomerization reaches a dynamic equilibrium, and the beta anomer could completely convert to the alpha anomer in the process of crystallization and precipitation. The acetylation of 4-chloro-4-deoxy-D-galactopyranose is kinetically controlled, and the configuration of the starting galactose determines the configuration of the resulting acetates. The influence of the chloro group at C-4 and the O-acetyl group at the anomeric carbon on the galactopyranose ring conformations is discussed, based upon the crystallographic data for the alpha and beta anomers of 1,2,3,6-tetra-O-acetyl-4-chloro-4-deoxy- D-galactopyranose. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.11.028
• 作为产物：
  描述：

  三氯蔗糖 在 氢氧化钾 作用下， 以 水 为溶剂， 反应 4.0h， 以89%的产率得到1,4:3,6-dianhydro-β-D-fructofuranosyl 4-chloro-4-deoxy-α-D-galactopyranoside
  参考文献：
  名称：

  一种从氯化蔗糖中脱水半乳糖蔗糖衍生物的简便方法

  摘要：

  三种新的脱水蔗糖衍生物：1,4：3,6-二脱水-β-D-果糖呋喃糖基4-氯-4-脱氧-α-D-吡喃半乳糖苷（4），1,4：3,6-二脱水-β-D -果糖呋喃糖基3,6-脱水-4-氯-4-脱氧-α-D-吡喃半乳糖苷（6）和1,6-二氯-1,6-二脱氧-β-D-呋喃呋喃糖基-3,6-脱水4由氯化蔗糖制备-氯-4-脱氧-α-D-吡喃半乳糖苷（8）。这些酸酐的结构通过其（1）H和（13）C NMR光谱，ESIMS和元素分析得到证实。给出了6的晶体结构和4（5）的乙酸盐。1,6-二氯-1,6-二脱氧-β-d-果呋喃呋喃糖基4,6-二氯-4,6-二脱氧-α-D-吡喃半乳糖苷中氯甲基对S（N）2反应的相对反应性为发现以6> 6'> 1'的顺序排列。

  DOI：

  10.1016/j.carres.2004.09.013

文献信息

• A facile approach to anhydrogalactosucrose derivatives from chlorinated sucrose
  作者：Feng-Wu Liu、Hong-Min Liu、Yu Ke、Jingyu Zhang

  DOI：10.1016/j.carres.2004.09.013

  日期：2004.11

  Three new anhydrosucrose derivatives: 1,4:3,6-dianhydro-beta-D-fructofuranosyl 4-chloro-4-deoxy-alpha-D-galactopyranoside (4), 1,4:3,6-dianhydro-beta-D-fructofuranosyl 3,6-anhydro-4-chloro-4-deoxy-alpha-D-galactopyranoside (6) and 1,6-dichloro-1,6-dideoxy-beta-D-fructofuranosyl-3,6-anhydro-4-chloro-4-deoxy-alpha-D-galactopyranoside (8) were prepared from chlorinated sucrose. The structures of these

  三种新的脱水蔗糖衍生物：1,4：3,6-二脱水-β-D-果糖呋喃糖基4-氯-4-脱氧-α-D-吡喃半乳糖苷（4），1,4：3,6-二脱水-β-D -果糖呋喃糖基3,6-脱水-4-氯-4-脱氧-α-D-吡喃半乳糖苷（6）和1,6-二氯-1,6-二脱氧-β-D-呋喃呋喃糖基-3,6-脱水4由氯化蔗糖制备-氯-4-脱氧-α-D-吡喃半乳糖苷（8）。这些酸酐的结构通过其（1）H和（13）C NMR光谱，ESIMS和元素分析得到证实。给出了6的晶体结构和4（5）的乙酸盐。1,6-二氯-1,6-二脱氧-β-d-果呋喃呋喃糖基4,6-二氯-4,6-二脱氧-α-D-吡喃半乳糖苷中氯甲基对S（N）2反应的相对反应性为发现以6> 6'> 1'的顺序排列。
• Preparation of α and β anomers of 1,2,3,6-tetra-O-acetyl-4-chloro-4-deoxy-d-galactopyranose based upon anomerization and kinetic acetylation
  作者：Feng-Wu Liu、Yan-Bing Zhang、Hong-Min Liu、Xiao-Ping Song

  DOI：10.1016/j.carres.2004.11.028

  日期：2005.2

  4-Chloro-4-deOXY-alpha-D-galactopyranose, 1,2,3,6-tetra-O-acetyl-4-chloro-4-deoxy-alpha-D-galactopyranose and 1,2,3,6-tetra-O-acetyl-4-chloro-4-deoxy-beta-D-galactopyranose were readily prepared from 1,4:3,6-dianhydro-beta-D-fructofuranosyl 4-chloro-4-deoxy-alpha- D-galactopyranoside. In the study, we found an interesting anomerization phenomenon of 4-chloro-4-deoxy-D-galactose. The molar ratio of alpha and beta anomers in solution is about 1:2 when the anomerization reaches a dynamic equilibrium, and the beta anomer could completely convert to the alpha anomer in the process of crystallization and precipitation. The acetylation of 4-chloro-4-deoxy-D-galactopyranose is kinetically controlled, and the configuration of the starting galactose determines the configuration of the resulting acetates. The influence of the chloro group at C-4 and the O-acetyl group at the anomeric carbon on the galactopyranose ring conformations is discussed, based upon the crystallographic data for the alpha and beta anomers of 1,2,3,6-tetra-O-acetyl-4-chloro-4-deoxy- D-galactopyranose. (C) 2005 Elsevier Ltd. All rights reserved.