O-α-D-glucopyranosyl-(1->3)-tris3)>-D-glucopyranose | 24885-56-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-α-D-glucopyranosyl-(1->3)-tris3)>-D-glucopyranose
• 英文别名: nigeropentaose；Glc(a1-3)Glc(a1-3)Glc(a1-3)Glc(a1-3)Glc；(3R,4S,5R,6R)-4-[(2R,3R,4S,5R,6R)-4-[(2R,3R,4S,5R,6R)-4-[(2R,3R,4S,5R,6R)-3,5-dihydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-(hydroxymethyl)oxane-2,3,5-triol
• CAS: 24885-56-1
• 化学式: C₃₀H₅₂O₂₆
• 分子量: 828.727
• InChiKey: UUQINGLDFWYORW-BGJXBHKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -9
• 重原子数：
  56
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  427
• 氢给体数：
  17
• 氢受体数：
  26

反应信息

• 作为产物：
  描述：

  O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->3)-tris3)>-1,2,4,6-tetra-O-acetyl-β-D-glucopyranose 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以95%的产率得到O-α-D-glucopyranosyl-(1->3)-tris3)>-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

文献信息

• Synthesis of nigero-oligosaccharides
  作者：Kenichi Takeo、Shinichi Kitamura、Yoshihiro Murata

  DOI：10.1016/0008-6215(92)84098-d

  日期：1992.2

  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.