(ξ-2-phenyl-[1,3]dioxan-5-yl)-[tetra-O-acetyl-β-D-glucopyranoside | 76222-76-9

• 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: (ξ-2-phenyl-[1,3]dioxan-5-yl)-[tetra-O-acetyl-β-D-glucopyranoside
• 英文别名: (ξ-2-Phenyl-[1,3]dioxan-5-yl)-[tetra-O-acetyl-β-D-glucopyranosid；2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl (1,3-benzylidene)glycerol；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(2-phenyl-1,3-dioxan-5-yl)oxy]oxan-2-yl]methyl acetate
• CAS: 76222-76-9
• 化学式: C₂₄H₃₀O₁₂
• 分子量: 510.495
• InChiKey: JRCALRXNXUDXSR-BTNZFBCUSA-N

物化性质

• 沸点：
  577.0±50.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  142
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (ξ-2-phenyl-[1,3]dioxan-5-yl)-[tetra-O-acetyl-β-D-glucopyranoside 在 palladium on activated charcoal 氢气 、 sodium methylate 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 生成 1,3-二羟基-2-丙基吡喃己糖苷
  参考文献：
  名称：

  Synthesis of Glycosyl Glycerols and Related Glycolipids

  摘要：

  Several isomeric glycosyl glycerols were synthesized. Acetylated allyl glycosides of D-glucose and D-galactose were transformed into 1-O-(glycopyranosyl)-rac-glycerols in a three step procedure via the corresponding 2,3-epoxypropyl glycosides and the peracetylated glycosyl glycerols. Tetra-O-benzyl-D-glucose was glycosylated with 1,3-di-O-benzylglycerol to give the alpha-anomer preferentially. The 2-O-(tetra-O-acetyl-beta-glycopyranosyl)-sn-glycerols and 2-O-(beta-glycopyranosyl)-sn-glycerols of D-glucose, D-galactose and N-acetyl-D-glucosamine and the corresponding alpha-derivatives of D-mannose were synthesized by selective glycosylation methods from 1,3-di-O-benzylglycerol and 1,3-O-benzylideneglycerol, respectively, and activated sugar compounds followed by hydrogenolysis. After long chain acylation and selective deacetylation the 1,3-di-O-acyl-2-O-(beta-glycopyranosyl)-sn-glycerols of D-glucose, D-galactose and N-acetyl-D-glucosamine and the corresponding a-derivative of D-mannose were synthesized.

  DOI：

  10.1080/07328309808007465
• 作为产物：
  描述：

  2-苯基-1,3-二氧六环-5-醇 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 碘 、 silver carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 120.0h， 以30%的产率得到(ξ-2-phenyl-[1,3]dioxan-5-yl)-[tetra-O-acetyl-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of Glycosyl Glycerols and Related Glycolipids

  摘要：

  Several isomeric glycosyl glycerols were synthesized. Acetylated allyl glycosides of D-glucose and D-galactose were transformed into 1-O-(glycopyranosyl)-rac-glycerols in a three step procedure via the corresponding 2,3-epoxypropyl glycosides and the peracetylated glycosyl glycerols. Tetra-O-benzyl-D-glucose was glycosylated with 1,3-di-O-benzylglycerol to give the alpha-anomer preferentially. The 2-O-(tetra-O-acetyl-beta-glycopyranosyl)-sn-glycerols and 2-O-(beta-glycopyranosyl)-sn-glycerols of D-glucose, D-galactose and N-acetyl-D-glucosamine and the corresponding alpha-derivatives of D-mannose were synthesized by selective glycosylation methods from 1,3-di-O-benzylglycerol and 1,3-O-benzylideneglycerol, respectively, and activated sugar compounds followed by hydrogenolysis. After long chain acylation and selective deacetylation the 1,3-di-O-acyl-2-O-(beta-glycopyranosyl)-sn-glycerols of D-glucose, D-galactose and N-acetyl-D-glucosamine and the corresponding a-derivative of D-mannose were synthesized.

  DOI：

  10.1080/07328309808007465

文献信息

• Carter, Chemische Berichte, 1930, vol. 63, p. 1684,1687
  作者：Carter

  DOI：——

  日期：——
• Franzen, Lars-Erik; Svensson, Sigfrid, Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1980, vol. 34, # 3, p. 171 - 176
  作者：Franzen, Lars-Erik、Svensson, Sigfrid

  DOI：——

  日期：——
• Synthesis of Glycosyl Glycerols and Related Glycolipids
  作者：René Suhr、Oliver Scheel、Joachim Thiem

  DOI：10.1080/07328309808007465

  日期：1998.8.1

  Several isomeric glycosyl glycerols were synthesized. Acetylated allyl glycosides of D-glucose and D-galactose were transformed into 1-O-(glycopyranosyl)-rac-glycerols in a three step procedure via the corresponding 2,3-epoxypropyl glycosides and the peracetylated glycosyl glycerols. Tetra-O-benzyl-D-glucose was glycosylated with 1,3-di-O-benzylglycerol to give the alpha-anomer preferentially. The 2-O-(tetra-O-acetyl-beta-glycopyranosyl)-sn-glycerols and 2-O-(beta-glycopyranosyl)-sn-glycerols of D-glucose, D-galactose and N-acetyl-D-glucosamine and the corresponding alpha-derivatives of D-mannose were synthesized by selective glycosylation methods from 1,3-di-O-benzylglycerol and 1,3-O-benzylideneglycerol, respectively, and activated sugar compounds followed by hydrogenolysis. After long chain acylation and selective deacetylation the 1,3-di-O-acyl-2-O-(beta-glycopyranosyl)-sn-glycerols of D-glucose, D-galactose and N-acetyl-D-glucosamine and the corresponding a-derivative of D-mannose were synthesized.