O-(3-O-allyl-2,4,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->3)-O-(2,4,6-tri-O-benzyl-α-D-glucopyranosyl)-1,2,4,6-tetra-O-acetyl-β-D-glucopyranose | 140420-90-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(3-O-allyl-2,4,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->3)-O-(2,4,6-tri-O-benzyl-α-D-glucopyranosyl)-1,2,4,6-tetra-O-acetyl-β-D-glucopyranose
• CAS: 140420-90-2
• 化学式: C₇₁H₈₀O₂₀
• 分子量: 1253.4
• InChiKey: WVVAXMLVJXEISG-QSBOOMAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.27
• 重原子数：
  91.0
• 可旋转键数：
  32.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  215.96
• 氢给体数：
  0.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  O-(3-O-allyl-2,4,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->3)-O-(2,4,6-tri-O-benzyl-α-D-glucopyranosyl)-1,2,4,6-tetra-O-acetyl-β-D-glucopyranose 在 sodium acetate 、 palladium dichloride 作用下， 以 水 、 溶剂黄146 为溶剂， 以80%的产率得到O-(2,4,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->3)-O-(2,4,6-tri-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
• 作为产物：
  描述：

  1,2,4,6-四-O-乙酰基-3-O-烯丙基-β-D-吡喃葡萄糖 在 sodium methylate 、 四氯化锡 、 sodium hydride 、 N,N-二甲基甲酰胺 作用下， 以 甲醇 、 1,2-二氯乙烷 、 paraffin 为溶剂， 反应 5.5h， 生成 O-(3-O-allyl-2,4,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->3)-O-(2,4,6-tri-O-benzyl-α-D-glucopyranosyl)-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