methyl 2,3-di-O-benzoyl-4,6-O-(4-methoxybenzylidene)-α-D-galactopyranoside | 273397-25-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: methyl 2,3-di-O-benzoyl-4,6-O-(4-methoxybenzylidene)-α-D-galactopyranoside
• 英文别名: [(2S,4aR,6S,7R,8S,8aS)-7-benzoyloxy-6-methoxy-2-(4-methoxyphenyl)-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-8-yl] benzoate
• CAS: 273397-25-4
• 化学式: C₂₉H₂₈O₉
• 分子量: 520.536
• InChiKey: ZQSLDTFWMCNNCZ-SWJKKVKRSA-N

物化性质

• 沸点：
  646.1±55.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  98.8
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl 2,3-di-O-benzoyl-4,6-O-(4-methoxybenzylidene)-α-D-galactopyranoside 在 4 A molecular sieve 、 sodium cyanoborohydride 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 以67%的产率得到methyl 2,3-di-O-benzoyl-6-O-(4-methoxybenzyl)-α-D-galactopyranoside
  参考文献：
  名称：

  Stereocontrolled preparation of 2-,3- and 4-isothiocyanato aldopyranose derivatives

  摘要：

  The regio- and stereocontrolled introduction of an isothiocyanato group into the positions 2, 3 and 4 of glycopyranose derivatives starting from glycosides, glycosylamines, and aminosugars is reported. Isothiocyanato sugars with D-gluco, D-allo and D-manno configurations have been prepared. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00212-3
• 作为产物：
  描述：

  苯甲酰氯 、 methyl 4,6-O-(4-methoxybenzylidene)-α-D-galactopyranoside 在 吡啶 作用下， 反应 12.0h， 以95%的产率得到methyl 2,3-di-O-benzoyl-4,6-O-(4-methoxybenzylidene)-α-D-galactopyranoside
  参考文献：
  名称：

  Stereocontrolled preparation of 2-,3- and 4-isothiocyanato aldopyranose derivatives

  摘要：

  The regio- and stereocontrolled introduction of an isothiocyanato group into the positions 2, 3 and 4 of glycopyranose derivatives starting from glycosides, glycosylamines, and aminosugars is reported. Isothiocyanato sugars with D-gluco, D-allo and D-manno configurations have been prepared. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00212-3

文献信息

• Regioselective Benzoylation of 4,6-<i>O</i>-Benzylidene Acetals of Glycopyranosides in the Presence of Transition Metals
  作者：Evgeny V. Evtushenko

  DOI：10.1080/07328303.2014.996291

  日期：2015.1.2

  Benzoylation of 4,6-O-benzylidene acetals of glycopyranosides by benzoic anhydride in acetonitrile in the presence of Cu(CF3COO)(2) as a promoter gave 2-benzoates for alpha-D-glucopyranosides and alpha-D-mannopyranosides and 3-benzoates for beta-D-galactopyranosides in good yields with high regioselectivity. Benzoylation of 4,6-O-benzylidene acetals of glycopyranosides of D-galactose and D-mannose by benzoyl chloride in the presence of MoO2(acac)(2) as a catalyst in all studied cases led to regioselective 3-O-substitution.
• Stereocontrolled preparation of 2-,3- and 4-isothiocyanato aldopyranose derivatives
  作者：Jose Fuentes、David Olano、Consolación Gasch、M Angeles Pradera

  DOI：10.1016/s0957-4166(00)00212-3

  日期：2000.6

  The regio- and stereocontrolled introduction of an isothiocyanato group into the positions 2, 3 and 4 of glycopyranose derivatives starting from glycosides, glycosylamines, and aminosugars is reported. Isothiocyanato sugars with D-gluco, D-allo and D-manno configurations have been prepared. (C) 2000 Elsevier Science Ltd. All rights reserved.