2,3,6,1’,3’,4’-hexa-O-acetylsucrose | 56038-06-3

• 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: 2,3,6,1’,3’,4’-hexa-O-acetylsucrose
• 英文别名: 2,3,6,1',3',4'-hexa-O-acetylsucrose；2,3,6,1',3',4'-Hexa-O-acetyl-sucrose；[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-6-[(2S,3S,4R,5R)-3,4-diacetyloxy-2-(acetyloxymethyl)-5-(hydroxymethyl)oxolan-2-yl]oxy-3-hydroxyoxan-2-yl]methyl acetate
• CAS: 56038-06-3
• 化学式: C₂₄H₃₄O₁₇
• 分子量: 594.524
• InChiKey: HMPQPOUTKLAYMW-IUYXUTJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  41
• 可旋转键数：
  17
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  226
• 氢给体数：
  2
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  2,3,6,1’,3’,4’-hexa-O-acetylsucrose 在 4-二甲氨基吡啶 、 四甲基乙二胺 、 3 A molecular sieve 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 生成 6'-O-(tri-O-methylgalloyl)-2,3,4,6,1',3',4'-hepta-O-acetylsucrose
  参考文献：
  名称：

  Fast Galloylation of a Sugar Moiety: Preparation of Three Monogalloylsucroses as References for Antioxidant Activity. A Method for the Selective Deprotection of tert-Butyldiphenylsilyl Ethers

  摘要：

  Three protected new gallotannins, namely the 6'-O-(tri-O-methylgalloyl)-2,3,4,6,1',3',4'-hepta-O-acetylsucrose, the 6'-O-(tri-O-methylgalloyl)-2,3,4,6,1',3',4'-hepta-O-benzoylsucrose and the 6,6'-di-O-tert-butyldiphenylsilyl-1'-O-(tri-O-methylgalloyl)-2,3,4,3',4'-penta-O-acetylsucrose have been prepared in four short sequences from sucrose. Methods for rapid galloylation have been studied in order to avoid simultaneous acyl transfer reactions. A method for the deprotection of a tert-butyldiphenylsilyl ether has been developed which avoids the intramolecular migration of a benzoate group. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00593-7
• 作为产物：
  描述：

  6,6'-di-O-tert-butyldiphenylsilyl-2,3,4,1',3',4'-hexa-O-acetylsucrose 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以79%的产率得到2,3,6,1’,3’,4’-hexa-O-acetylsucrose
  参考文献：
  名称：

  Fast Galloylation of a Sugar Moiety: Preparation of Three Monogalloylsucroses as References for Antioxidant Activity. A Method for the Selective Deprotection of tert-Butyldiphenylsilyl Ethers

  摘要：

  Three protected new gallotannins, namely the 6'-O-(tri-O-methylgalloyl)-2,3,4,6,1',3',4'-hepta-O-acetylsucrose, the 6'-O-(tri-O-methylgalloyl)-2,3,4,6,1',3',4'-hepta-O-benzoylsucrose and the 6,6'-di-O-tert-butyldiphenylsilyl-1'-O-(tri-O-methylgalloyl)-2,3,4,3',4'-penta-O-acetylsucrose have been prepared in four short sequences from sucrose. Methods for rapid galloylation have been studied in order to avoid simultaneous acyl transfer reactions. A method for the deprotection of a tert-butyldiphenylsilyl ether has been developed which avoids the intramolecular migration of a benzoate group. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00593-7

文献信息

• Aqueous Glycosylation of Unprotected Sucrose Employing Glycosyl Fluorides in the Presence of Calcium Ion and Trimethylamine
  作者：Guillaume Pelletier、Aaron Zwicker、C. Liana Allen、Alanna Schepartz、Scott J. Miller

  DOI：10.1021/jacs.5b13384

  日期：2016.3.9

  synthetic glycosylation reaction between sucrosyl acceptors and glycosyl fluoride donors to yield the derived trisaccharides. This reaction proceeds at room temperature in an aqueous solvent mixture. Calcium salts and a tertiary amine base promote the reaction with high site-selectivity for either the 3'-position or 1'-position of the fructofuranoside unit. Because nonenzymatic aqueous oligosaccharide syntheses

  我们报告了蔗糖基受体和糖基氟供体之间的合成糖基化反应，产生衍生的三糖。该反应在室温下在水性溶剂混合物中进行。钙盐和叔胺碱促进反应，对呋喃果糖苷单元的 3'-位或 1'-位具有高位点选择性。由于非酶水性寡糖合成尚不成熟，因此进行了机理研究，以确定选择性的起源，我们假设这与蔗糖中羟基阵列的结构有关。各种单脱氧蔗糖类似物的溶液构象揭示了羟基在同时介导这种水性糖基键形成反应和位点选择性方面的协同性质。