methyl O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside | 140420-85-5

• 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-benzyl-α-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside
• 英文别名: Bn(-2)[Bn(-3)][Bn(-4)][Bn(-6)]Glc(a1-3)[Bn(-2)][Bn(-4)][Bn(-6)]Glc(b)-SMe；(2S,3R,4S,5R,6R)-2-methylsulfanyl-3,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxane
• CAS: 140420-85-5
• 化学式: C₆₂H₆₆O₁₀S
• 分子量: 1003.27
• InChiKey: GIFFLUOMCDYDAZ-NYOKHUAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  73
• 可旋转键数：
  26
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  methyl O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 在 palladium on activated charcoal 、 4 A molecular sieve 、 四丁基溴化铵 、 氢气 、 N,N-二甲基甲酰胺 、 copper(ll) bromide 作用下， 以 乙二醇甲醚 、 1,2-二氯乙烷 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 96.0h， 生成 Acetic acid (2S,3R,4S,5R,6R)-2,5-diacetoxy-6-acetoxymethyl-4-[(2R,3R,4S,5R,6R)-3,5-dihydroxy-6-hydroxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-3-yl ester
  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：

  溴甲苯 、 methyl O-α-D-glucopyranosyl-(1->3)-1-thio-β-D-glucopyranoside 在 sodium hydride 、 N,N-二甲基甲酰胺 作用下， 生成 methyl O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-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

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.