4-(N-acetamido)phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside | 75705-23-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(N-acetamido)phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• 英文别名: 4-acetylaminophenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside；N-Acetyl-p-aminophenol-tetraacetyl-β-D-glucopyranosid；[(2R,3R,4S,5R,6S)-6-(4-acetamidophenoxy)-3,4,5-triacetyloxyoxan-2-yl]methyl acetate
• CAS: 75705-23-6
• 化学式: C₂₂H₂₇NO₁₁
• 分子量: 481.456
• InChiKey: ZVFAHCKHVUBNMZ-QMCAAQAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  34
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  153
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  4-(N-acetamido)phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 在 二正丁基氧化锡 作用下， 以 甲醇 为溶剂， 反应 10.0h， 以82.3%的产率得到4-(N-acetamido)phenyl β-D-glucopyranoside
  参考文献：
  名称：

  用温和的选择性方法用二丁基氧化锡裂解O-乙酰基

  摘要：

  已经开发了一种温和有效的中性方法，用于用二丁基氧化锡裂解O-乙酰基。该方法在合成含有碱敏感或酸敏感的多功能基团的糖苷中特别有用。

  DOI：

  10.1016/s0008-6215(02)00277-x
• 作为产物：
  描述：

  对乙酰氨基酚 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 potassium carbonate 作用下， 反应 1.0h， 以82%的产率得到4-(N-acetamido)phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Solvent-Free Mechanochemical Synthesis of Aryl Glycosides^[1]

  摘要：

  Aryl glycosides have been prepared from a range of readily available glycosyl halides by a solvent-free mechanochemical procedure employing a planetary ball mill in excellent yields. Besides being a solvent-free reaction, the procedure has been successful in eliminating the need for employing any phase-transfer catalyst in the reaction.

  DOI：

  10.1080/07328300802402259

文献信息

• FeCl3-promoted and ultrasound-assisted synthesis of resveratrol O-derived glycoside analogs
  作者：Hamid Marzag、Guillaume Robert、Maeva Dufies、Khalid Bougrin、Patrick Auberger、Rachid Benhida

  DOI：10.1016/j.ultsonch.2014.05.022

  日期：2015.1

  Phenol derived O-glycosides were synthesized using a direct and convenient O-glycosidation, starting from acetylated sugars in the presence of FeCl3, an inexpensive, mild and benign Lewis acid catalyst. The reactions were carried out under both conventional and ultrasonic irradiation conditions. In general, improvement in rates and yields were observed when reactions were carried out under sonication compared with conventional conditions leading to the corresponding beta-O-glycosides as the major anomer. Post-synthetic transformations of iodophenol intermediates led to new resveratrol O-glycoside analogs in good overall yields. (C) 2014 Elsevier B.V. All rights reserved.