methyl O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-acetyl-1-thio-β-D-glucopyranoside | 140420-83-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-acetyl-1-thio-β-D-glucopyranoside
• 英文别名: Glc2Ac3Ac4Ac6Ac(a1-3)Glc2Ac4Ac6Ac(b)-SMe；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(2R,3R,4S,5R,6S)-3,5-diacetyloxy-2-(acetyloxymethyl)-6-methylsulfanyloxan-4-yl]oxyoxan-2-yl]methyl acetate
• CAS: 140420-83-3
• 化学式: C₂₇H₃₈O₁₇S
• 分子量: 666.655
• InChiKey: YEUAKMPIKPHNQJ-STCAYSEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  45
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  237
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  methyl O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-acetyl-1-thio-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.67h， 以95%的产率得到methyl O-α-D-glucopyranosyl-(1->3)-1-thio-β-D-glucopyranoside
  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 、 2,4,6-三甲基吡啶 、 palladium on activated charcoal 、 氢气 、 silver perchlorate 、 四氯化锡 、 溶剂黄146 作用下， 以 乙二醇二甲醚 、 乙醚 、 乙二醇甲醚 、 1,2-二氯乙烷 为溶剂， 25.0~70.0 ℃ 、101.33 kPa 条件下， 反应 6.33h， 生成 methyl O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-acetyl-1-thio-β-D-glucopyranoside
  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