5-(methoxycarbonyl)pentyl 2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside | 1296782-02-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃二恶英
• 英文名称: 5-(methoxycarbonyl)pentyl 2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside
• 英文别名: 5-(methoxycarbonyl)pentyl 2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside；methyl 6-[[(2S,4aR,6S,7R,8R,8aR)-7-azido-8-hydroxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]hexanoate
• CAS: 1296782-02-9
• 化学式: C₂₀H₂₇N₃O₇
• 分子量: 421.45
• InChiKey: JJEKYBFZVYOQED-KXMHTTHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  30
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  97.8
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  5-(methoxycarbonyl)pentyl 2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside 、 2,3,4,6-tetra-O-benzoyl-D-galactopyranosyl trichloroacetimidate 在 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以74%的产率得到5-(methoxycarbonyl)pentyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->3)-2-azido-4,6-O-benzylidene-2-deoxy-α-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of the carbohydrate moiety from the parasite Echinococcus multilocularis and their antigenicity against human sera

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2011.02.030
• 作为产物：
  描述：

  5-(methoxycarbonyl)pentyl-3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-galactopyranoside 在 camphor-10-sulfonic acid 、 sodium methylate 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 3.5h， 生成 5-(methoxycarbonyl)pentyl 2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of the carbohydrate moiety from the parasite Echinococcus multilocularis and their antigenicity against human sera

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2011.02.030

文献信息

• Synthesis, Antigenicity Against Human Sera and Structure-Activity Relationships of Carbohydrate Moieties from Toxocara larvae and Their Analogues
  作者：Akihiko Koizumi、Kimiaki Yamano、Takashi Tsuchiya、Frank Schweizer、Fumiyuki Kiuchi、Noriyasu Hada

  DOI：10.3390/molecules17089023

  日期：——

  Stereocontrolled syntheses of biotin-labeled oligosaccharide portions containing the Galβ1-3GalNAc core of the TES-glycoprotein antigen obtained from larvae of the parasite Toxocara and their analogues have been accomplished. Trisaccharides Fuc2Meα1-2Gal4Meβ1-3GalNAcα1-OR (A), Fucα1-2Gal4Meβ1-3GalNAcα1-OR (B), Fuc2Meα1-2Galβ1-3GalNAcα1-OR (C), Fucα1-2Galβ1-3GalNAcα1-OR (D) and a disaccharide Fuc2Meα1-2Gal4Meβ1-OR

  已经完成了生物素标记的寡糖部分的立体控制合成，该部分包含从寄生虫弓首蛔虫及其类似物的幼虫获得的 TES-糖蛋白抗原的 Galβ1-3GalNAc 核心。三糖 Fuc2Meα1-2Gal4Meβ1-3GalNAcα1-OR (A), Fucα1-2Gal4Meβ1-3GalNAcα1-OR (B), Fuc2Meα1-2Galβ1-3GalNAcα1-OR (C), Fucα1-2GalNAcα1-OR (C), Fucα1-2Galβ1-2Galβ1-2Galβ1-2Gal二糖 (A) -OR (E) (R = 生物素化探针) 使用 5-(甲氧基羰基) 戊基-2,3,4,6-四-O-乙酰基-β-D-吡喃半乳糖基-(1→3)-通过嵌段合成合成2-azide-4-O-benzyl-2-deoxy-α-D-galactopyranoside 作为常见的糖基受体。我们通过酶联免疫吸附试验 (ELISA)