2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl-(1'->2C)-2-C-(hydroxymethyl)-1-methyl-2,3-O-isopropylidene-D-erythrofuranoside | 936555-88-3

• 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',4',6'-tetra-O-acetyl-β-D-galactopyranosyl-(1'->2C)-2-C-(hydroxymethyl)-1-methyl-2,3-O-isopropylidene-D-erythrofuranoside
• CAS: 936555-88-3
• 化学式: C₂₃H₃₄O₁₄
• 分子量: 534.515
• InChiKey: HVVVGDCRTPSTQS-SUTOXMHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.02
• 重原子数：
  37.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  160.58
• 氢给体数：
  0.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl-(1'->2C)-2-C-(hydroxymethyl)-1-methyl-2,3-O-isopropylidene-D-erythrofuranoside 在 Dowex H⁽¹⁺⁾ resin 、 水 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 β-D-galactopyranosyl-(1->2C)-2-C-(hydroxymethyl)-D-erythrose
  参考文献：
  名称：

  A Disaccharide Rearrangement Catalyzed by Molybdate Anion in Aqueous Solution

  摘要：

  Reaction of a galactosylated 2-C-(hydroxymethyl)-tetrofuranose with paramolybdate ion-exchange resin in aqueous solution at 67 degrees C gave an equililibrium mixture containing the reactant aldofuranose (42%) and a 2-ketopentofuranose galactosylated at O1 (58%). Observation of this stereospecific rearrangement supports prior arguments that substituents at C2 of the branched-chain aldofuranose reactant are located in a sterically accessible pocket of the putative dimolybdate-saccharide reactive complex during epimerization. This rearrangement provides a new and convenient route to 2-ketosugars glycosylated at the exocyclic C1 position.

  DOI：

  10.1021/jo062494+
• 作为产物：
  描述：

  methyl 2-C-(hydroxymethyl)-2,3-O-isopropylidene-D-erythrofuranoside 、 2,3,4,6-四乙酰氧基-alpha-D-吡喃糖溴化物 在 氰化汞 作用下， 以 硝基甲烷 、 二氯甲烷 为溶剂， 反应 6.0h， 以85%的产率得到2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl-(1'->2C)-2-C-(hydroxymethyl)-1-methyl-2,3-O-isopropylidene-D-erythrofuranoside
  参考文献：
  名称：

  A Disaccharide Rearrangement Catalyzed by Molybdate Anion in Aqueous Solution

  摘要：

  Reaction of a galactosylated 2-C-(hydroxymethyl)-tetrofuranose with paramolybdate ion-exchange resin in aqueous solution at 67 degrees C gave an equililibrium mixture containing the reactant aldofuranose (42%) and a 2-ketopentofuranose galactosylated at O1 (58%). Observation of this stereospecific rearrangement supports prior arguments that substituents at C2 of the branched-chain aldofuranose reactant are located in a sterically accessible pocket of the putative dimolybdate-saccharide reactive complex during epimerization. This rearrangement provides a new and convenient route to 2-ketosugars glycosylated at the exocyclic C1 position.

  DOI：

  10.1021/jo062494+