p-Chlorphenyl-β-D-galactosid-tetraacetat | 2872-70-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-Chlorphenyl-β-D-galactosid-tetraacetat
• 英文别名: (4-chloro-phenyl)-(tetra-O-acetyl-β-D-galactopyranoside)；(4-Chlor-phenyl)-(tetra-O-acetyl-β-D-galactopyranosid)；[(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-(4-chlorophenoxy)oxan-2-yl]methyl acetate
• CAS: 2872-70-0
• 化学式: C₂₀H₂₃ClO₁₀
• 分子量: 458.85
• InChiKey: SALMOSOXXNZOJP-LCWAXJCOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  p-Chlorphenyl-β-D-galactosid-tetraacetat 在 六甲基二硅烷 、 碘 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以90%的产率得到(2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-(4-chlorophenoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  碘-六甲基乙硅烷（HMDS）介导的过乙酰化1,2-反式连接的烷基和芳基糖苷的异构化

  摘要：

  已经发现在HMDS存在下用碘处理过乙酰化的烷基和芳基1，2-反式-糖苷会导致异构化，从而导致形成相应的1，2-顺式-糖苷。在具有短烷基链长的糖苷配基的烷基糖苷的情况下，观察到完全糖化为α-糖苷，而对于那些具有较长链长的糖苷，发现该过程是不完全的。这些观察已被机械地解释了。

  DOI：

  10.1016/j.carres.2010.02.012
• 作为产物：
  描述：

  对氯苯酚 、 beta-D-半乳糖五乙酸酯 在 aluminium-<4-chloro-phenolate> 作用下， 生成 p-Chlorphenyl-β-D-galactosid-tetraacetat
  参考文献：
  名称：

  Über eine neue Synthese von Phenolglykosiden

  摘要：

  DOI：

  10.1002/ardp.19542870109

文献信息

• Phase-transfer-catalyzed synthesis of 2,3,4,6-tetra-O-acetyl-β-d-galactopyranosides
  作者：Henry P. Kleine、David V. Weinberg、Robert J. Kaufman、Ravinder S. Sidhu

  DOI：10.1016/0008-6215(85)85036-9

  日期：1985.10
• Stereoselective single-step synthesis and X-ray crystallographic investigation of acetylated aryl 1,2-trans glycopyranosides and aryl 1,2-cis C2-hydroxy-glycopyranosides
  作者：Udayanath Aich、Duraikkannu Loganathan

  DOI：10.1016/j.carres.2005.10.010

  日期：2006.1

  Reported is an attractive and environmentally friendly method for the synthesis of the title compounds in moderate yield using inexpensive 1,2,3,4,6-penta-O-acetyl-beta-D-gluco- and galactopyranoses as sugar donors, five different phenols as acceptors and H-beta zeolite as the catalyst. The yield (23-28%) of aryl 3,4,6-tri-O-acetyl-alpha-D-glycopyranosides obtained in this single-step procedure is considerably higher than that obtained using previously reported methods. Treatment of an orthoacetate, 3,4,6-tri-O-acetyl-[1,2-O-(1-p-fluorophenoxyethylidene)]-alpha-D-glucopyranose, with p-fluorophenol under the same solvent-free reaction conditions also led to the formation of the title compounds in similar yield and composition. X-ray crystallographic analysis of phenyl 3,4,6-tri-O-acetyl-alpha-D-glucopyranoside and p-fluorophenyl 3,4,6-tri-O-acetyl-alpha-D-glucopyranoside showed that the molecular packing is stabilized by C-H center dot center dot center dot O, C-H center dot center dot center dot pi and C-H center dot center dot center dot F interactions, in addition to regular hydrogen bonding patterns. (c) 2005 Elsevier Ltd. All rights reserved.