2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-galactopyranosyl-(1->3)-1,2,5,6-tetra-O-acetyl-α,β-D-galactofuranose | 313360-61-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-galactopyranosyl-(1->3)-1,2,5,6-tetra-O-acetyl-α,β-D-galactofuranose
• 英文别名: Bn(-2)[Bn(-3)][Bn(-4)][Bn(-6)]Gal(a1-6)[Bn(-2)][Bn(-3)][Bn(-4)]Gal(a1-3)Galf1Ac2Ac5Ac6Ac；[(2R)-2-acetyloxy-2-[(2S,3S,4R)-4,5-diacetyloxy-3-[(2R,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-[[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyoxolan-2-yl]ethyl] acetate
• CAS: 313360-61-1
• 化学式: C₇₅H₈₂O₂₀
• 分子量: 1303.46
• InChiKey: GMPNCXMIZCETSC-LXOSNMCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.1
• 重原子数：
  95
• 可旋转键数：
  37
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  216
• 氢给体数：
  0
• 氢受体数：
  20

反应信息

• 作为反应物：
  描述：

  ethyl 2,4-di-O-benzyl-6-O-chloroacetyl-α-D-mannopyranosyl-(1->3)-2,4,6-tri-O-benzyl-1-thio-α-D-mannopyranoside 、 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-galactopyranosyl-(1->3)-1,2,5,6-tetra-O-acetyl-α,β-D-galactofuranose 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以85%的产率得到ethyl 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-galactopyranosyl-(1->3)-2,5,6-tri-O-acetyl-β-D-galactofuranosyl-(1->3)-2,4-di-O-Bn-6-O-chloroacetyl-α-D-mannopyranosyl-(1->3)-2,4,6-tri-O-Bn-1-thio-α-D-mannopyranoside
  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
• 作为产物：
  描述：

  乙基-2,3,4,6-O-四苄基-Beta-D-硫代半乳糖苷 在 4 A molecular sieve 、 四乙基溴化铵 、 溴 、 DMTST 作用下， 以 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 53.08h， 生成 2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-galactopyranosyl-(1->3)-1,2,5,6-tetra-O-acetyl-α,β-D-galactofuranose
  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