methyl 4-O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-2,3-O-isopropylidene-aldehydo-D-glucuronate dimethyl acetal | 466680-66-0

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: methyl 4-O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-2,3-O-isopropylidene-aldehydo-D-glucuronate dimethyl acetal
• CAS: 466680-66-0
• 化学式: C₃₅H₄₈O₁₃
• 分子量: 676.758
• InChiKey: RDUWMTOFOBPXQD-PEBZVAKKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.09
• 重原子数：
  48.0
• 可旋转键数：
  15.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  138.83
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  methyl 4-O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-2,3-O-isopropylidene-aldehydo-D-glucuronate dimethyl acetal 在 palladium dihydroxide 氢气 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以100%的产率得到methyl 4-O-(3,4-O-isopropylidene-β-D-galactopyranosyl)-2,3-O-isopropylidene-aldehydo-D-glucuronate dimethyl acetal
  参考文献：
  名称：

  Chemical transformation of lactose into 4-O-β-d-galactopyranosyl-d-glucuronic acid (pseudolactobiouronic acid) and some derivatives thereof

  摘要：

  The selective oxidation of the primary alcoholic function of the reducing unit of lactose was achieved in good overall yield (67%) starting from 2',6'-di-O-benzyl-2,3:3',4'-di-O-isopropylidenelactose dimethyl acetal (1) through a simple multi-step procedure based on the selective acetylation of OH-5 of 1 (methoxyisopropylation, acetylation, de-methoxyisopropylation) followed by a two-step oxidation at C-6 (TPAP-NMO then TEMPO-NaOCl) and finally, complete removal of the protecting groups. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00084-8
• 作为产物：
  描述：

  Acetic acid (1R,2R)-2-((3aS,4R,6S,7R,7aS)-7-benzyloxy-4-benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-2-((4S,5R)-5-dimethoxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-1-(2-methoxy-propoxymethyl)-ethyl ester 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 4 Angstroem MS 、 sodium methylate 、 4-甲基苯磺酸吡啶 、 碳酸氢钠 、 potassium bromide 作用下， 以 甲醇 、 乙醚 、 乙酸乙酯 为溶剂， 反应 3.25h， 生成 methyl 4-O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-2,3-O-isopropylidene-aldehydo-D-glucuronate dimethyl acetal
  参考文献：
  名称：

  Chemical transformation of lactose into 4-O-β-d-galactopyranosyl-d-glucuronic acid (pseudolactobiouronic acid) and some derivatives thereof

  摘要：

  The selective oxidation of the primary alcoholic function of the reducing unit of lactose was achieved in good overall yield (67%) starting from 2',6'-di-O-benzyl-2,3:3',4'-di-O-isopropylidenelactose dimethyl acetal (1) through a simple multi-step procedure based on the selective acetylation of OH-5 of 1 (methoxyisopropylation, acetylation, de-methoxyisopropylation) followed by a two-step oxidation at C-6 (TPAP-NMO then TEMPO-NaOCl) and finally, complete removal of the protecting groups. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(02)00084-8