methyl (2,3-di-O-acetyl-3-C-(benzyloxymethyl)-β-D-erythrofuranosyl)-(1->2) (methyl 3,4-O-isopropylidene-α-D-galactopyranosid)uronate | 801320-31-0

• 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) (methyl 3,4-O-isopropylidene-α-D-galactopyranosid)uronate
• CAS: 801320-31-0
• 化学式: C₂₇H₃₆O₁₃
• 分子量: 568.575
• InChiKey: XBVPKPJNLHDSCA-BKNWOVDUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.24
• 重原子数：
  40.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  143.51
• 氢给体数：
  0.0
• 氢受体数：
  13.0

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) (methyl 3,4-O-isopropylidene-α-D-galactopyranosid)uronate 在 palladium diacetate 氢气 、 sodium methylate 作用下， 以 甲醇 、 溶剂黄146 、 乙酸乙酯 为溶剂， 20.0 ℃ 、303.37 kPa 条件下， 反应 36.0h， 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：

  p-tolyl 2,3-di-O-acetyl-3-C-(benzyloxymethyl)-1-thio-α-D-erythrofuranoside 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 N-碘代丁二酰亚胺 、 四丁基氟化铵 、 四丁基氯化铵 、 silver trifluoromethanesulfonate 、 potassium bromide 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 5.67h， 生成 methyl (2,3-di-O-acetyl-3-C-(benzyloxymethyl)-β-D-erythrofuranosyl)-(1->2) (methyl 3,4-O-isopropylidene-α-D-galactopyranosid)uronate
  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