ethyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl-(1->2)-bis[4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl]-(1->2)-4-azido-3-O-benzyl-4,6-dideoxy-1-thio-α-D-mannopyranoside | 848828-36-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl-(1->2)-bis[4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl]-(1->2)-4-azido-3-O-benzyl-4,6-dideoxy-1-thio-α-D-mannopyranoside
• CAS: 848828-36-4
• 化学式: C₅₄H₆₆N₁₂O₁₂S
• 分子量: 1107.26
• InChiKey: YOWZHPSZAIPBJL-GQQXTPTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.29
• 重原子数：
  79.0
• 可旋转键数：
  24.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  316.8
• 氢给体数：
  1.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  ethyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl-(1->2)-bis[4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl]-(1->2)-4-azido-3-O-benzyl-4,6-dideoxy-1-thio-α-D-mannopyranoside 、 碘甲烷 在 氢氧化钾 作用下， 以 二甲基亚砜 为溶剂， 反应 1.0h， 以89%的产率得到ethyl 4-azido-3-O-benzyl-4,6-dideoxy-2-O-methyl-α-D-mannopyranosyl-(1->2)-bis[4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl]-(1->2)-4-azido-3-O-benzyl-4,6-dideoxy-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Immunogens from a synthetic hexasaccharide fragment of the O-SP of Vibrio cholerae O:1, serotype Ogawa

  摘要：

  The known 5-(methoxycarbonyl)pentyl alpha-glycoside of the hexasaccharide of Vibrio cholerae O:1, serotype Ogawa 24 was newly prepared. The efficiency of construction of the hexasaccharide from the disaccharide glycosyl acceptor 6 and each of the two tetrasaccharide glycosyl donors 16, and 18, as an alternative to the iterative coupling of the disaccharide glycosyl donor 7 with 6, was evaluated. Compound 24 was treated with each of hydrazine hydrate, ethylenediamine. and hexamethylenediamine to give ligands 25, 27, and 29, respectively, equipped with different linkers. Reaction of the foregoing compounds with squaric acid diethyl ester. and the reactions of the thus formed monoesters 26, 28, and 30 with BSA were evaluated. The rate of formation of the corresponding monoester was higher with hydrazide 25 than with amines 27 and 29. whose reaction rates were virtually the same. Reactions of squaric acid derivatives 26, 28, and 30 with BSA were conducted under the same conditions (reaction temperature, ligand-BSA ratio, and concentration with respect to the hapten) and targeted for neoglycoconjugates with 24-BSA ratio of similar to5. Monitoring the conversions by SELDI-TOF mass spectrometry in conjunction with the ProteinChip(R) system made it possible to conduct the conjugations in controlled fashion, and to terminate the reactions when the desired carbohydrate-protein ratios were reached. Products from 26, 28, and 30, neoglycoconjugates 31-33, containing 4.9, 5.0, and 5.1 moles of 24/BSA, respectively, were obtained in 87-93% yields. When the conjugation started with the initial molar carbohydrate-protein ratio of 15:1, the final molar carbohydrate-BSA ratio reached after 14 days with ligands 26, 28, and 30 was 9.0, 11.0, and 9.1, respectively. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.021
• 作为产物：
  描述：

  ethyl 2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl-(1->2)(4-azido-3-O-benzyl-4,6-dideoxy-1-thio-α-D-mannopyranoside 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 0.25h， 生成 ethyl 4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl-(1->2)-bis[4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl]-(1->2)-4-azido-3-O-benzyl-4,6-dideoxy-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Immunogens from a synthetic hexasaccharide fragment of the O-SP of Vibrio cholerae O:1, serotype Ogawa

  摘要：

  The known 5-(methoxycarbonyl)pentyl alpha-glycoside of the hexasaccharide of Vibrio cholerae O:1, serotype Ogawa 24 was newly prepared. The efficiency of construction of the hexasaccharide from the disaccharide glycosyl acceptor 6 and each of the two tetrasaccharide glycosyl donors 16, and 18, as an alternative to the iterative coupling of the disaccharide glycosyl donor 7 with 6, was evaluated. Compound 24 was treated with each of hydrazine hydrate, ethylenediamine. and hexamethylenediamine to give ligands 25, 27, and 29, respectively, equipped with different linkers. Reaction of the foregoing compounds with squaric acid diethyl ester. and the reactions of the thus formed monoesters 26, 28, and 30 with BSA were evaluated. The rate of formation of the corresponding monoester was higher with hydrazide 25 than with amines 27 and 29. whose reaction rates were virtually the same. Reactions of squaric acid derivatives 26, 28, and 30 with BSA were conducted under the same conditions (reaction temperature, ligand-BSA ratio, and concentration with respect to the hapten) and targeted for neoglycoconjugates with 24-BSA ratio of similar to5. Monitoring the conversions by SELDI-TOF mass spectrometry in conjunction with the ProteinChip(R) system made it possible to conduct the conjugations in controlled fashion, and to terminate the reactions when the desired carbohydrate-protein ratios were reached. Products from 26, 28, and 30, neoglycoconjugates 31-33, containing 4.9, 5.0, and 5.1 moles of 24/BSA, respectively, were obtained in 87-93% yields. When the conjugation started with the initial molar carbohydrate-protein ratio of 15:1, the final molar carbohydrate-BSA ratio reached after 14 days with ligands 26, 28, and 30 was 9.0, 11.0, and 9.1, respectively. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.021