methyl 3-O-benzyl-5,6-O-isopropylidene-β-D-galactofuranosyl-(1->5)-2,3,6-tri-O-benzyl-β-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzyl-β-D-galactofuranoside | 920274-38-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 3-O-benzyl-5,6-O-isopropylidene-β-D-galactofuranosyl-(1->5)-2,3,6-tri-O-benzyl-β-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzyl-β-D-galactofuranoside
• 英文别名: (2R,3R,4R,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-[(1R)-1-[(2S,3S,4R,5R)-5-[(2R)-2-[(2S,3S,4R,5R)-5-methoxy-3,4-bis(phenylmethoxy)oxolan-2-yl]-2-phenylmethoxyethoxy]-3,4-bis(phenylmethoxy)oxolan-2-yl]-2-phenylmethoxyethoxy]-4-phenylmethoxyoxolan-3-ol
• CAS: 920274-38-0
• 化学式: C₇₁H₈₀O₁₆
• 分子量: 1189.41
• InChiKey: LTOOPMFGFPMEFN-KMHVJNLESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  87
• 可旋转键数：
  31
• 环数：
  11.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  159
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  、 methyl 3-O-benzyl-5,6-O-isopropylidene-β-D-galactofuranosyl-(1->5)-2,3,6-tri-O-benzyl-β-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzyl-β-D-galactofuranoside 在 2,6-二叔丁基-4-甲基吡啶 、 4 A molecular sieve 、 trifluoromethanesulfonic acid anhydride 作用下， 以 二氯甲烷 为溶剂， 反应 24.33h， 以75%的产率得到methyl 2,3-anhydro-5,6-di-O-benzoyl-α-D-gulofuranosyl-(1->2)-3-O-benzyl-5,6-O-isopropylidene-β-D-galactofuranosyl-(1->5)-2,3,6-tri-O-benzyl-β-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzyl-β-D-galactofuranoside
  参考文献：
  名称：

  Synthesis of a Pentasaccharide Fragment of Varianose, a Cell Wall Polysaccharide from Penicillium varians

  摘要：

  The first synthesis of an oligosaccharide fragment of varianose, a polysaccharide produced by Penicillium varians, is reported. The target pentasaccharide features both alpha- and beta-galactofuranoside residues and the alpha-galactofuranoside residue is hindered, being substituted on adjacent oxygens (O1 and O2), both of which are cis to the two-carbon side chain at C4. Key features of the synthesis include a novel method for the selective protection of the C3 hydroxyl group of galactofuranosyl residues via an epoxide formation/opening sequence, the introduction of the alpha-D-galactofuranosyl residue using a 2,3-anhydrosugar donor, and the use of the 1-benzenesulfinylpiperidine/trifluoromethanesulfonic anhydride activation method for the addition of an alpha-D-glucopyranosyl residue to a hindered hydroxyl group in an advanced tetrasaccharide intermediate.

  DOI：

  10.1021/jo061821a
• 作为产物：
  描述：

  methyl 2,3,5-tri-O-benzyl-β-D-galactofuranoside 在 N-碘代丁二酰亚胺 、 偶氮二甲酸二异丙酯 、 4 A molecular sieve 、 sodium methylate 、 silver trifluoromethanesulfonate 、 二正丁基氧化锡 、 溶剂黄146 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 、 苯甲醇 为溶剂， 反应 89.16h， 生成 methyl 3-O-benzyl-5,6-O-isopropylidene-β-D-galactofuranosyl-(1->5)-2,3,6-tri-O-benzyl-β-D-galactofuranosyl-(1->6)-2,3,5-tri-O-benzyl-β-D-galactofuranoside
  参考文献：
  名称：

  Synthesis of a Pentasaccharide Fragment of Varianose, a Cell Wall Polysaccharide from Penicillium varians

  摘要：

  The first synthesis of an oligosaccharide fragment of varianose, a polysaccharide produced by Penicillium varians, is reported. The target pentasaccharide features both alpha- and beta-galactofuranoside residues and the alpha-galactofuranoside residue is hindered, being substituted on adjacent oxygens (O1 and O2), both of which are cis to the two-carbon side chain at C4. Key features of the synthesis include a novel method for the selective protection of the C3 hydroxyl group of galactofuranosyl residues via an epoxide formation/opening sequence, the introduction of the alpha-D-galactofuranosyl residue using a 2,3-anhydrosugar donor, and the use of the 1-benzenesulfinylpiperidine/trifluoromethanesulfonic anhydride activation method for the addition of an alpha-D-glucopyranosyl residue to a hindered hydroxyl group in an advanced tetrasaccharide intermediate.

  DOI：

  10.1021/jo061821a

文献信息

• Synthesis of a Pentasaccharide Fragment of Varianose, a Cell Wall Polysaccharide from <i>Penicillium varians</i>
  作者：Yu Bai、Todd L. Lowary

  DOI：10.1021/jo061821a

  日期：2006.12.1

  The first synthesis of an oligosaccharide fragment of varianose, a polysaccharide produced by Penicillium varians, is reported. The target pentasaccharide features both alpha- and beta-galactofuranoside residues and the alpha-galactofuranoside residue is hindered, being substituted on adjacent oxygens (O1 and O2), both of which are cis to the two-carbon side chain at C4. Key features of the synthesis include a novel method for the selective protection of the C3 hydroxyl group of galactofuranosyl residues via an epoxide formation/opening sequence, the introduction of the alpha-D-galactofuranosyl residue using a 2,3-anhydrosugar donor, and the use of the 1-benzenesulfinylpiperidine/trifluoromethanesulfonic anhydride activation method for the addition of an alpha-D-glucopyranosyl residue to a hindered hydroxyl group in an advanced tetrasaccharide intermediate.