5-(methoxycarbonyl)pentyl 2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside | 566934-68-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(methoxycarbonyl)pentyl 2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside
• 英文别名: 5-methoxycarbonylpentyl 2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside；methyl 6-[(2S,3S,4S,5R,6R)-3-acetyloxy-5-azido-6-methyl-4-phenylmethoxyoxan-2-yl]oxyhexanoate
• CAS: 566934-68-7
• 化学式: C₂₂H₃₁N₃O₇
• 分子量: 449.504
• InChiKey: FXVDDXPPYPHJRC-OUQVEZOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  32
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  94.6
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  5-(methoxycarbonyl)pentyl 2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside 在 N-碘代丁二酰亚胺 、 4 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 生成 5-(methoxycarbonyl)pentyl 2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl-(1->2)-4-azido-3-O-benzyl-4,6-dideoxy-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：

  6-羟基己酸甲酯 、 ethyl 2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-1-thio-α-D-mannopyranoside 在 N-碘代丁二酰亚胺 、 4 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以79%的产率得到5-(methoxycarbonyl)pentyl 2-O-acetyl-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranoside
  参考文献：
  名称：

  来自合成的四糖和六糖的新糖缀合物，模仿霍乱弧菌O：1血清型Inaba的O-PS末端。

  摘要：

  已经制备了具有已连接的N-3-脱氧-L-甘油-四氢电子酸侧链的糖基受体和糖基供体，并将其用于合成模仿O-的上游端的六糖的二通。霍乱弧菌O：1血清型Inaba的特定多糖。使用方酸二酯化学方法将以5-甲氧基羰基戊基糖苷形式获得的目标四糖和六糖与BSA连接。通过表面增强的激光解吸电离飞行时间质谱仪（SELDI-TOF MS）监测共轭反应。当达到所需的半抗原/ BSA摩尔比时，这可以控制合成寡糖的结合过程，并终止反应，产生具有预定碳水化合物/载体比的新糖缀合物。通过SELDI-TOF MS技术监测结合的能力，使得在一锅反应中从一个半抗原中制备出几种具有不同预定碳水化合物/载体比的新糖结合物成为可能。

  DOI：

  10.1039/b211660j