O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->3)-1,2,4,6-tetra-O-acetyl-β-D-glucopyranose | 140420-82-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->3)-1,2,4,6-tetra-O-acetyl-β-D-glucopyranose
• 英文别名: 3-O-(2,3,4,6-Tetra-O-benzyl-a-D-glucopyranosyl)-1,2,4,6-tetra-O-acetyl-b-D-glucopyranose；[(2R,3R,4S,5R,6S)-3,5,6-triacetyloxy-4-[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 140420-82-2
• 化学式: C₄₈H₅₄O₁₅
• 分子量: 870.948
• InChiKey: LXLVZNXEYURWIV-BGSAPFNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  63
• 可旋转键数：
  24
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  170
• 氢给体数：
  0
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->3)-1,2,4,6-tetra-O-acetyl-β-D-glucopyranose 在 吡啶 、 palladium on activated charcoal 、 氢气 作用下， 以 乙二醇甲醚 为溶剂， 反应 1.0h， 生成 O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->3)-1,2,4,6-tetra-O-acetyl-β-D-glucopyranose
  参考文献：
  名称：

  Synthesis of nigero-oligosaccharides

  摘要：

  Nigerose [alpha-D-Glcp-(1 --> 3)-D-Glcp], nigerotriose, nigerotetraose, and nigeropentaose have been synthesized by chain elongation starting at the reducing end, from the corresponding octa-, undeca-, tetradeca-, and heptadeca-beta-D-acetates, respectively, via thioglycoside-mediated 1,2-cis coupling, using 1,2,4,6-tetra-O-acetyl-beta-D-glucopyranose as the glucosyl acceptor and methyl 2,3,4,6-tetra-O-benzyl-1-thio-beta-D-glucopyranoside, methyl 3-O-allyl-2,4,6-tri-O-benzyl-1-thio-beta-D-glucopyranoside, and methyl O-(2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranosyl)-(1 --> 3)-2,4,6-tri-O-benzyl-1-thio-beta-D-glucopyranoside as the donors.

  DOI：

  10.1016/0008-6215(92)84098-d
• 作为产物：
  描述：

  3-O-benzyl-D-glucopyranose 在 吡啶 、 palladium on activated charcoal 、 4 A molecular sieve 、 四丁基溴化铵 、 氢气 、 溶剂黄146 、 N,N-二甲基甲酰胺 、 copper(ll) bromide 作用下， 25.0 ℃ 、101.33 kPa 条件下， 反应 1.33h， 生成 O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->3)-1,2,4,6-tetra-O-acetyl-β-D-glucopyranose
  参考文献：
  名称：

  Synthesis of nigero-oligosaccharides

  摘要：

  Nigerose [alpha-D-Glcp-(1 --> 3)-D-Glcp], nigerotriose, nigerotetraose, and nigeropentaose have been synthesized by chain elongation starting at the reducing end, from the corresponding octa-, undeca-, tetradeca-, and heptadeca-beta-D-acetates, respectively, via thioglycoside-mediated 1,2-cis coupling, using 1,2,4,6-tetra-O-acetyl-beta-D-glucopyranose as the glucosyl acceptor and methyl 2,3,4,6-tetra-O-benzyl-1-thio-beta-D-glucopyranoside, methyl 3-O-allyl-2,4,6-tri-O-benzyl-1-thio-beta-D-glucopyranoside, and methyl O-(2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranosyl)-(1 --> 3)-2,4,6-tri-O-benzyl-1-thio-beta-D-glucopyranoside as the donors.

  DOI：

  10.1016/0008-6215(92)84098-d