ethyl 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzyl-1-thio-β-D-galactopyranoside | 143995-72-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzyl-1-thio-β-D-galactopyranoside
• 英文别名: Bn(-2)[Bn(-3)][Bn(-4)][Bn(-6)]Gal(a1-6)[Bn(-2)][Bn(-3)][Bn(-4)]Gal(b)-SEt；(2S,3R,4S,5S,6R)-2-ethylsulfanyl-3,4,5-tris(phenylmethoxy)-6-[[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxymethyl]oxane
• CAS: 143995-72-6
• 化学式: C₆₃H₆₈O₁₀S
• 分子量: 1017.29
• InChiKey: LYUPOUIRTDYSGF-PKKNGMHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.6
• 重原子数：
  74
• 可旋转键数：
  27
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.33
• 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：

  allyl 2-O-acetyl-4-O-benzyl-6-O-tert-butyldiphenylsilyl-α-D-mannopyranoside 、 ethyl 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzyl-1-thio-β-D-galactopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 N,N-二甲基甲酰胺 作用下， 以 噻吩 、 甲苯 为溶剂， 以83%的产率得到
  参考文献：
  名称：

  多种糖基磷脂酰肌醇糖脂的一般和收敛合成†

  摘要：

  糖基磷脂酰肌醇（GPI）糖脂将大量蛋白质锚定在真核细胞的细胞膜中。他们保守的假五糖核心携带额外的磷酸乙醇胺，糖和脂质取代基。这些结构变异是物种或组织的特征，但其功能意义仍然未知。将特定功能与结构独特的GPI相关联的研究依赖于这些糖脂均质样品的可用性。为了满足这一需求，我们已经开发出通用的GPI糖脂合成途径。我们的聚合合成始于常见的结构单元，并依赖于一组完全正交的保护基团，该保护基团使得能够选择性引入磷酸二酯并有效组装GPI聚糖。在这里，我们报告了这种合成策略的发展，有关磷酸化方法的一组保护基团的评估，GPI聚糖的组装计划的评估，

  DOI：

  10.1039/c2sc21515b
• 作为产物：
  描述：

  1-硫代-Β-D-乙基半乳糖苷 在 吡啶 、 4-二甲氨基吡啶 、 四乙基溴化铵 、 sodium hydride 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 100.0h， 生成 ethyl 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzyl-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of the Leishmania LPG Core Heptasaccharyl myo-Inositol

  摘要：

  Total synthesis of the core heptasaccharyl myo-inositol, Galp(alpha1-6)Galp(alpha1-3)Galf(beta1-3)[Glcp(alpha1-PO4-6)Manp](alpha1-3)Manp(alpha1-4)GlcNp(alpha1-6)Ins-1-PO4, and the corresponding hexasaccharyl myo-inositol, Galp(alpha1-6)Galp(alpha1-3)Galf(beta1-3)Manp(alpha1-3)Manp(alpha1-4)GlcNp(alpha1-6)Ins-1-PO4, found in the lipophosphoglycans of Leishmania parasites are described. The target molecules contain synthetic challenges such as an unusual internal galactofuranosyl residue and an anomeric phosphodiester. The synthesis was accomplished using a convergent block synthetic strategy. Four building blocks, a trigalactoside, a dimannoside, a glucosyl inositolphosphate, and a glucosyl-alpha -1-H-phosphonate, all appropriately protected, were used. The trigalactoside was linked to the dimannoside followed by glycosylation with the glucosyl inositolphosphate to produce the fully protected hexasaccharyl myo-inositol. Subsequent oxidative coupling of the glucosyl-H-phosphonate formed the anomeric phosphodiester linkage to produce the protected heptasaccharyl myo-inositol. Both the assembly order of the subunits and sequence of deprotection were essential for the successful synthesis of these complex molecules. The deprotection was accomplished by deacetylation and clevage of benzyl ethers with sodium in liquid ammonia, followed by acidic deacetalization/desilylation to produce the target molecules.

  DOI：

  10.1021/ja001515t

文献信息

• A general and convergent synthesis of diverse glycosylphosphatidylinositol glycolipids
  作者：Yu-Hsuan Tsai、Sebastian Götze、Ivan Vilotijevic、Maurice Grube、Daniel Varon Silva、Peter H. Seeberger

  DOI：10.1039/c2sc21515b

  日期：——

  GPI glycolipids. Our convergent synthesis starts from common building blocks and relies on a fully orthogonal set of protecting groups that enables the regioselective introduction of phosphodiesters and efficient assembly of the GPI glycans. Here, we report on the development of this synthetic strategy, evaluation of the set of protecting groups with respect to phosphorylation methods, evaluation of

  糖基磷脂酰肌醇（GPI）糖脂将大量蛋白质锚定在真核细胞的细胞膜中。他们保守的假五糖核心携带额外的磷酸乙醇胺，糖和脂质取代基。这些结构变异是物种或组织的特征，但其功能意义仍然未知。将特定功能与结构独特的GPI相关联的研究依赖于这些糖脂均质样品的可用性。为了满足这一需求，我们已经开发出通用的GPI糖脂合成途径。我们的聚合合成始于常见的结构单元，并依赖于一组完全正交的保护基团，该保护基团使得能够选择性引入磷酸二酯并有效组装GPI聚糖。在这里，我们报告了这种合成策略的发展，有关磷酸化方法的一组保护基团的评估，GPI聚糖的组装计划的评估，
• Synthesis of the <i>Leishmania</i> LPG Core Heptasaccharyl <i>myo</i>-Inositol
  作者：Katinka Ruda、Jan Lindberg、Per J. Garegg、Stefan Oscarson、Peter Konradsson

  DOI：10.1021/ja001515t

  日期：2000.11.1

  Total synthesis of the core heptasaccharyl myo-inositol, Galp(alpha1-6)Galp(alpha1-3)Galf(beta1-3)[Glcp(alpha1-PO4-6)Manp](alpha1-3)Manp(alpha1-4)GlcNp(alpha1-6)Ins-1-PO4, and the corresponding hexasaccharyl myo-inositol, Galp(alpha1-6)Galp(alpha1-3)Galf(beta1-3)Manp(alpha1-3)Manp(alpha1-4)GlcNp(alpha1-6)Ins-1-PO4, found in the lipophosphoglycans of Leishmania parasites are described. The target molecules contain synthetic challenges such as an unusual internal galactofuranosyl residue and an anomeric phosphodiester. The synthesis was accomplished using a convergent block synthetic strategy. Four building blocks, a trigalactoside, a dimannoside, a glucosyl inositolphosphate, and a glucosyl-alpha -1-H-phosphonate, all appropriately protected, were used. The trigalactoside was linked to the dimannoside followed by glycosylation with the glucosyl inositolphosphate to produce the fully protected hexasaccharyl myo-inositol. Subsequent oxidative coupling of the glucosyl-H-phosphonate formed the anomeric phosphodiester linkage to produce the protected heptasaccharyl myo-inositol. Both the assembly order of the subunits and sequence of deprotection were essential for the successful synthesis of these complex molecules. The deprotection was accomplished by deacetylation and clevage of benzyl ethers with sodium in liquid ammonia, followed by acidic deacetalization/desilylation to produce the target molecules.