methyl (2,3-di-O-acetyl-3-C-(benzyloxymethyl)-β-D-erythrofuranosyl)-(1->2)-3,4-O-isopropylidene-α-D-galactopyranoside | 801320-29-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (2,3-di-O-acetyl-3-C-(benzyloxymethyl)-β-D-erythrofuranosyl)-(1->2)-3,4-O-isopropylidene-α-D-galactopyranoside
• CAS: 801320-29-6
• 化学式: C₂₆H₃₆O₁₂
• 分子量: 540.565
• InChiKey: INPHMDYZLAOGFE-GVWGJPDKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.06
• 重原子数：
  38.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  137.44
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  methyl (2,3-di-O-acetyl-3-C-(benzyloxymethyl)-β-D-erythrofuranosyl)-(1->2)-3,4-O-isopropylidene-α-D-galactopyranoside 在 palladium diacetate 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 四丁基氯化铵 、 氢气 、 sodium methylate 、 potassium bromide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 溶剂黄146 、 乙酸乙酯 为溶剂， 20.0 ℃ 、303.37 kPa 条件下， 反应 37.0h， 生成 methyl ((3-C-hydroxymethyl)-β-D-erythrofuranosyl)-(1->2)-α-D-galactopyranosiduronic acid
  参考文献：
  名称：

  Synthesis of a disaccharide fragment of rhamnogalacturonan II

  摘要：

  A disaccharide portion of the A-side chain of the rhamnogalacturonan II oligosaccharide has been prepared. Glycosylation of methyl (methyl 3,4-O-isopropylidene-alpha-D-galactopyranosid)uronate with p-tolyl 2,3-di-O-acetyl-3-C-(benzyloxymethyl)-1-thio-alpha/beta-D-erythrofuranoside was carried out using N-iodosuccinimide as promoter and silver trifluoromethanesulfonate as catalyst. Removal of the protecting groups gave the beta-D-Apif-(1-->2)-alpha-D-GalpA-OMe disaccharide. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.08.004
• 作为产物：
  描述：

  methyl 3,4-O-isopropylidene-6-O-tert-butyldiphenylsilyl-α-D-galactopyranoside 在 N-碘代丁二酰亚胺 、 四丁基氟化铵 、 silver trifluoromethanesulfonate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.67h， 生成 methyl (2,3-di-O-acetyl-3-C-(benzyloxymethyl)-β-D-erythrofuranosyl)-(1->2)-3,4-O-isopropylidene-α-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of a disaccharide fragment of rhamnogalacturonan II

  摘要：

  A disaccharide portion of the A-side chain of the rhamnogalacturonan II oligosaccharide has been prepared. Glycosylation of methyl (methyl 3,4-O-isopropylidene-alpha-D-galactopyranosid)uronate with p-tolyl 2,3-di-O-acetyl-3-C-(benzyloxymethyl)-1-thio-alpha/beta-D-erythrofuranoside was carried out using N-iodosuccinimide as promoter and silver trifluoromethanesulfonate as catalyst. Removal of the protecting groups gave the beta-D-Apif-(1-->2)-alpha-D-GalpA-OMe disaccharide. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.08.004