ethyl 2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-1-α-D-thiomannopyranoside | 866322-01-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-1-α-D-thiomannopyranoside
• 英文别名: Bz(-2)[Bn(-3)][Bn(-4)][Bn(-6)]Man(a1-6)[Bn(-2)][Bn(-3)][Bn(-4)]Man(a)-SEt；[(2S,3S,4S,5R,6R)-2-[[(2R,3R,4S,5S,6R)-6-ethylsulfanyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]methoxy]-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] benzoate
• CAS: 866322-01-2
• 化学式: C₆₃H₆₆O₁₁S
• 分子量: 1031.28
• InChiKey: NLSXYSHENZPPDO-SCAGXAJNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.8
• 重原子数：
  75
• 可旋转键数：
  27
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  135
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  ethyl 2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-1-α-D-thiomannopyranoside 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以90%的产率得到ethyl O-(3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->6)-2,3,4-tri-O-benzyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  锥虫LPPG七糖肌醇的合成

  摘要：

  在克氏锥虫脂肽磷酸聚糖中发现的七糖基肌醇的合成是使用三个构建块的会聚组装完成的。目标化合物是第一个要合成的与糖基磷脂酰肌醇锚定家族相关的完整 2-氨基乙基膦酸取代聚糖。组装顺序能够合成与 Tr 中其他糖基肌醇磷脂相关的磷酸肌醇寡糖。cruzi，一种引起南美洲流行的南美锥虫病的原生动物寄生虫。

  DOI：

  10.1021/ja057339b
• 作为产物：
  描述：

  ethyl 2-O-benzoyl-3,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside 在 溴 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 0.83h， 生成 ethyl 2-O-benzoyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-1-α-D-thiomannopyranoside
  参考文献：
  名称：

  Synthesis of the Core Tetrasaccharide of Trypanosoma cruzi Glycoinositolphospholipids: Manp(α1→6)-Manp(α1→4)-6-(2-aminoethylphosphonic acid)-GlcNp(α1→6)-myo-Ins-1-PO₄

  摘要：

  Synthesis of the core tetrasaccharide Manp(alpha 1 -> 6)-Manp((alpha 1 -> 4)-6-(2-aminoethylphosphonic acid)GlcNp((alpha 1 -> 6)-myo-Ins-1-PO4, found in glycoinositolphospholipids of Trypanosoma cruzi parasites, is described. The key building block, 6-0-(2-azido-3-0-benzyl-6-0-((2-benzyloxycarbonylaminoethyl)phosphonic acid benzyl ester)-2-deoxy-alpha-D-glueopyranosyl)-1-di-O-benzylphosphoryl-4,5-O-isopropylidene-2,3-O-(D-1,7,7-trimethyl[2,2,1]bicyclohept-6-ylidene)-D-Myo-inositol, was synthesized using a partially protected glucosyl D-camphorinositolphosphate and a (2-benzyloxycarbonylaminoethyl)phosphonic acid derivative in a regioselective phosphonate esterfication. Elongation with ethyl 2-O-benzoyl-3,4,6-tri-O-benzyl-alpha-D-mannopyranosyl-(1 -> 6)-2,3,4-tri-O-benzyl-l-alpha-D-thiomannopyrano- side using dimethyl(methylthio)sulfonium trifluoromethanesulfonate gave A fully protected tetrasaccharide which was successfully deprotected subsequently with sodium methoxide, sodium in liquid ammonia, and aq hydrochloric acid to give title compound.

  DOI：

  10.1021/jo0508595

文献信息

• Synthesis of the Core Tetrasaccharide of <i>Trypanosoma </i><i>c</i><i>ruzi</i> Glycoinositolphospholipids: Man<i>p</i>(α1→6)-Man<i>p</i>(α1→4)-6-(2-aminoethylphosphonic acid)-GlcN<i>p</i>(α1→6)-<i>m</i><i>yo</i>-Ins-1-PO₄
  作者：Markus Hederos、Peter Konradsson

  DOI：10.1021/jo0508595

  日期：2005.9.1

  Synthesis of the core tetrasaccharide Manp(alpha 1 -> 6)-Manp((alpha 1 -> 4)-6-(2-aminoethylphosphonic acid)GlcNp((alpha 1 -> 6)-myo-Ins-1-PO4, found in glycoinositolphospholipids of Trypanosoma cruzi parasites, is described. The key building block, 6-0-(2-azido-3-0-benzyl-6-0-((2-benzyloxycarbonylaminoethyl)phosphonic acid benzyl ester)-2-deoxy-alpha-D-glueopyranosyl)-1-di-O-benzylphosphoryl-4,5-O-isopropylidene-2,3-O-(D-1,7,7-trimethyl[2,2,1]bicyclohept-6-ylidene)-D-Myo-inositol, was synthesized using a partially protected glucosyl D-camphorinositolphosphate and a (2-benzyloxycarbonylaminoethyl)phosphonic acid derivative in a regioselective phosphonate esterfication. Elongation with ethyl 2-O-benzoyl-3,4,6-tri-O-benzyl-alpha-D-mannopyranosyl-(1 -> 6)-2,3,4-tri-O-benzyl-l-alpha-D-thiomannopyrano- side using dimethyl(methylthio)sulfonium trifluoromethanesulfonate gave A fully protected tetrasaccharide which was successfully deprotected subsequently with sodium methoxide, sodium in liquid ammonia, and aq hydrochloric acid to give title compound.
• Synthesis of the <i>Trypanosoma </i><i>c</i><i>ruzi</i> LPPG Heptasaccharyl <i>m</i><i>yo</i>-Inositol
  作者：Markus Hederos、Peter Konradsson

  DOI：10.1021/ja057339b

  日期：2006.3.1

  lipopeptidophosphoglycan was accomplished using a convergent assembly of three building blocks. The target compound is the first complete 2-aminoethyl phosphonic acid substituted glycan related to the glycosylphosphatidylinositol anchor family to be synthesized. The order of assembly enables synthesis of phosphoinositol oligosaccharides related to other glycosylinositolphospholipids in Tr. cruzi, the

  在克氏锥虫脂肽磷酸聚糖中发现的七糖基肌醇的合成是使用三个构建块的会聚组装完成的。目标化合物是第一个要合成的与糖基磷脂酰肌醇锚定家族相关的完整 2-氨基乙基膦酸取代聚糖。组装顺序能够合成与 Tr 中其他糖基肌醇磷脂相关的磷酸肌醇寡糖。cruzi，一种引起南美洲流行的南美锥虫病的原生动物寄生虫。