N-(2,2-dimethoxyethyl)-6-[2-O-methyl-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl-(1->2)-tetrakis(4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl)-(1->2)-(4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl)oxy]hexanamide | 260360-37-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: N-(2,2-dimethoxyethyl)-6-[2-O-methyl-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl-(1->2)-tetrakis(4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl)-(1->2)-(4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl)oxy]hexanamide
• CAS: 260360-37-0
• 化学式: C₈₉H₁₁₃N₁₉O₂₂
• 分子量: 1800.99
• InChiKey: GRAZAFQFWGMWHX-CWYBDYKWSA-N

反应信息

• 作为反应物：
  描述：

  N-(2,2-dimethoxyethyl)-6-[2-O-methyl-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl-(1->2)-tetrakis(4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl)-(1->2)-(4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl)oxy]hexanamide 在 硫化氢 作用下， 以 吡啶 、 水 为溶剂， 以81%的产率得到N-(2,2-dimethoxyethyl)-6-[4-amino-3-O-benzyl-4,6-dideoxy-2-O-methyl-α-D-mannopyranosyl-(1->2)-tetrakis(4-amino-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl)-(1->2)-(4-amino-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl)oxy]hexanamide
  参考文献：
  名称：

  Studies on vaccines against cholera. Synthesis of neoglycoconjugates from the hexasaccharide determinant of Vibriocholerae O:1, serotype Ogawa, by single-point attachment or by attachment of the hapten in the form of clusters

  摘要：

  The terminal hexasaccharide of the O-antigen of Vibrio cholerae O:1, serotype Ogawa, has been synthesized in the form of a glycoside whose aglycon (linker) allows conjugation to carrier proteins by reductive amination. The conjugate obtained from direct, single-point attachment of the linker-equipped hapten to chicken serum albumin (CSA) contained seven hapten residues/CSA. A neoglycoconjugate containing the carbohydrate antigen in the form of clusters was obtained using, as a hapten subcarrier, an oligopeptide containing 16 amino groups. It was treated with a limited amount of hapten, to give a hapten-carrying subcarrier (HCS). Subsequent conjugation of HCS to CSA, using squaric acid diethyl ester as a conjugation reagent, gave a cross-linked, glycocluster conjugate containing 51% (w/w) of the carbohydrate. Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(99)00185-8
• 作为产物：
  描述：

  N-(2,2-dimethoxyethyl)-6-[4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl-(1->2)-tetrakis(4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl)-(1->2)-(4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl)oxy]hexanamide 、 碘甲烷 在 silver(l) oxide 作用下， 生成 N-(2,2-dimethoxyethyl)-6-[2-O-methyl-4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl-(1->2)-tetrakis(4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl)-(1->2)-(4-azido-3-O-benzyl-4,6-dideoxy-α-D-mannopyranosyl)oxy]hexanamide
  参考文献：
  名称：

  Studies on vaccines against cholera. Synthesis of neoglycoconjugates from the hexasaccharide determinant of Vibriocholerae O:1, serotype Ogawa, by single-point attachment or by attachment of the hapten in the form of clusters

  摘要：

  The terminal hexasaccharide of the O-antigen of Vibrio cholerae O:1, serotype Ogawa, has been synthesized in the form of a glycoside whose aglycon (linker) allows conjugation to carrier proteins by reductive amination. The conjugate obtained from direct, single-point attachment of the linker-equipped hapten to chicken serum albumin (CSA) contained seven hapten residues/CSA. A neoglycoconjugate containing the carbohydrate antigen in the form of clusters was obtained using, as a hapten subcarrier, an oligopeptide containing 16 amino groups. It was treated with a limited amount of hapten, to give a hapten-carrying subcarrier (HCS). Subsequent conjugation of HCS to CSA, using squaric acid diethyl ester as a conjugation reagent, gave a cross-linked, glycocluster conjugate containing 51% (w/w) of the carbohydrate. Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(99)00185-8