phenyl 2-O-benzoyl-3,6-di-O-benzyl-4-O-chloroacetyl-1-thio-β-D-galactopyranoside | 1163124-33-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: phenyl 2-O-benzoyl-3,6-di-O-benzyl-4-O-chloroacetyl-1-thio-β-D-galactopyranoside
• CAS: 1163124-33-1
• 化学式: C₃₅H₃₃ClO₇S
• 分子量: 633.162
• InChiKey: FQQSIOTYPJODGQ-DMTSBHICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.68
• 重原子数：
  44.0
• 可旋转键数：
  13.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl 2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside 、 phenyl 2-O-benzoyl-3,6-di-O-benzyl-4-O-chloroacetyl-1-thio-β-D-galactopyranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以79%的产率得到2-(trimethylsilyl)ethyl 2-O-benzoyl-3,6-di-O-benzyl-4-O-chloroacetyl-β-D-galactopyranosyl-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside
  参考文献：
  名称：

  Synthetic studies on the carbohydrate moiety of the antigen from the parasite Echinococcusmultilocularis

  摘要：

  Stereocontrolled syntheses of branched tri-, tetra-, and pentasaccharides displaying a Gal beta 1 -> 3GalNAc core in the glycan portion of the glycoprotein antigen from the parasite Echinococcus multilocularis have been accomplished. Trisaccharide Gal beta 1 -> 3(GlcNAc beta 1 -> 6)GalNAc alpha 1-OR (A). tetrasaccharide Gal beta 1 -> 3(Gal beta 1 -> 4Gal beta 1 -> 6)GalNac alpha 1-OR(D), and pentasaccharides Gal beta 1 -> 3(Gal beta 1 -> 4Gal beta 1 -> 4Gl cNAc beta 1-6)GalNAc alpha 1-OR (E) and Gal beta 1-3(Gal alpha 1 -> 4Gal alpha 1 -> 4Gal alpha 1 -> 6)GalNAc alpha 1-OR) (F) (R = 2(trimethylsilyl)ethyl) were synthesized by block synthesis. The disaccharide 2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-acetyl-P-D-galactopyranosyl-(1 -> 3)-2-azido-4-O-benzyl-2-deoxy-alpha-D-galactopyranoside served as a common glycosyl acceptor in the synthesis of the branched oligosaccharicles. Moreover, linear trisaccharide Gal beta 1 -> Gal beta 1 -> 3GalNac alpha 1-OR (B) and branched tetrasaccharide Gal beta 1 -> Gal beta 1 -> 3(GalNac beta 1 -> 6)GalNac alpha 1-OR (C) were synthesized by stepwise condensation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.02.019
• 作为产物：
  描述：

  phenyl 3,6-di-O-benzyl-2-O-benzoyl-1-thio-β-D-galactopyranoside 、 氯乙酰氯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以86%的产率得到phenyl 2-O-benzoyl-3,6-di-O-benzyl-4-O-chloroacetyl-1-thio-β-D-galactopyranoside
  参考文献：
  名称：

  Synthetic studies on the carbohydrate moiety of the antigen from the parasite Echinococcusmultilocularis

  摘要：

  Stereocontrolled syntheses of branched tri-, tetra-, and pentasaccharides displaying a Gal beta 1 -> 3GalNAc core in the glycan portion of the glycoprotein antigen from the parasite Echinococcus multilocularis have been accomplished. Trisaccharide Gal beta 1 -> 3(GlcNAc beta 1 -> 6)GalNAc alpha 1-OR (A). tetrasaccharide Gal beta 1 -> 3(Gal beta 1 -> 4Gal beta 1 -> 6)GalNac alpha 1-OR(D), and pentasaccharides Gal beta 1 -> 3(Gal beta 1 -> 4Gal beta 1 -> 4Gl cNAc beta 1-6)GalNAc alpha 1-OR (E) and Gal beta 1-3(Gal alpha 1 -> 4Gal alpha 1 -> 4Gal alpha 1 -> 6)GalNAc alpha 1-OR) (F) (R = 2(trimethylsilyl)ethyl) were synthesized by block synthesis. The disaccharide 2-(trimethylsilyl)ethyl 2,3,4,6-tetra-O-acetyl-P-D-galactopyranosyl-(1 -> 3)-2-azido-4-O-benzyl-2-deoxy-alpha-D-galactopyranoside served as a common glycosyl acceptor in the synthesis of the branched oligosaccharicles. Moreover, linear trisaccharide Gal beta 1 -> Gal beta 1 -> 3GalNac alpha 1-OR (B) and branched tetrasaccharide Gal beta 1 -> Gal beta 1 -> 3(GalNac beta 1 -> 6)GalNac alpha 1-OR (C) were synthesized by stepwise condensation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2009.02.019

文献信息

• Synthesis of the Carbohydrate Moiety of Glycoproteins from the Parasite Echinococcus granulosus and Their Antigenicity against Human Sera
  作者：Noriyasu Hada、Tokio Morita、Takashi Ueda、Kazuki Masuda、Hiromi Nakane、Mami Ogane、Kimiaki Yamano、Frank Schweizer、Fumiyuki Kiuchi

  DOI：10.3390/molecules26185652

  日期：——

  6-O-benzylidene-2-deoxy-α-d-galactopyranoside as a common glycosyl acceptor. The synthesis of the tetrasaccharide and the pentasaccharide was improved from the viewpoint of reducing the number of synthetic steps and increasing the total yield by changing from stepwise condensation to block synthesis. Moreover, hexasaccharide E, which contains the oligosaccharide sequence which occurs in E. granulosus

  含有细粒棘球绦虫糖蛋白碳水化合物部分的生物素标记寡糖部分的立体控制合成已经完成。三糖 Galβ1-3Galβ1-3GalNAcα1-R ( A )、四糖 Galα1-4Galβ1-3Galβ1-3GalNAcα1-R ( B ) 和五糖 Galα1-4Galβ1-3Galβ1-3Galβ1-3GalNAcα1-R ( C )，（R = 生物素化探针）使用5-(甲氧基羰基)戊基2-叠氮基-4,6- O-亚苄基-2-脱氧-α- d-吡喃半乳糖苷作为常见糖基受体，通过逐步缩合和/或嵌段合成法合成。通过从逐步缩合变为嵌段合成，从减少合成步骤数和增加总收率的角度来看，改进了四糖和五糖的合成。此外，由三糖D合成了六糖E ，其含有细粒棘球绦虫中存在的寡糖序列。我们通过酶联免疫吸附测定（ELISA）检查了这五种寡糖的抗原性。虽然C – E化合物对囊性包虫病 (CE) 患者血清不表现出抗原性，但化合物B 、
• Synthesis of the carbohydrate moiety from the parasite Echinococcus multilocularis and their antigenicity against human sera
  作者：Akihiko Koizumi、Kimiaki Yamano、Frank Schweizer、Tadahiro Takeda、Fumiyuki Kiuchi、Noriyasu Hada

  DOI：10.1016/j.ejmech.2011.02.030

  日期：2011.5

  Stereocontrolled syntheses of biotin-labeled oligosaccharide portions with a Gal beta 1-3GalNAc core of the Em2 glycoprotein antigen obtained from the parasite Echinococcus multilocularis have been accomplished. Trisaccharide Gal beta 1-3(GlcNAc beta 1-6)GalNAc alpha 1-R (G), tetrasaccharide Gal beta 1-3(Gal beta 1-4GlcNAc beta 1-6)GalNAc alpha 1-R (I) and pentasaccharide Gal beta 1-3(Gal alpha 1-4Gal beta 1-4GlcNAc beta 1-6)GalNAc alpha 1-R (K) (R = biotinylated probe) were synthesized by block synthesis by the use of 5-(methoxycarbonyl)pentyl 2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl-(1 -> 3)-2-azido-4-O-benzyl-2-deoxy-alpha-D-galactopyranoside as a common glycosyl acceptor. Moreover, linear trisaccharide Gal alpha 1-4Gal beta 1-3GalNAc alpha 1-R (H) and branched tetrasaccharide Gal alpha 1-4Gal beta 1-3(GlcNAc beta 1-6)GalNAc alpha 1-R (1) were synthesized by stepwise wise condensation. We examined the antigenicity of these five oligosaccharides by an enzyme linked immunosorbent assay (ELISA). Our results demonstrate that biotinylated oligosaccharides H, I and K show good serodiagnostic potential to detect infections caused by the parasite E. multilocularis. Among them the linear sequence Gal alpha 1-4Gal beta 1-3GalNAc alpha 1-R in oligosaccharide (H) appears to show the highest sensitivity (95%). Moreover, our study clarified the dominant carbohydrate epitope of Em2 antigen. (C) 2011 Elsevier Masson SAS. All rights reserved.