8-methoxycarbonyloctyl 3-O-benzoyl-4,6-O-cyclohexylidene-2-O-(tetra-O-benzyl-α-D-galactopyranosyl)-α-D-mannopyranoside | 82086-26-8

• 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: 8-methoxycarbonyloctyl 3-O-benzoyl-4,6-O-cyclohexylidene-2-O-(tetra-O-benzyl-α-D-galactopyranosyl)-α-D-mannopyranoside
• CAS: 82086-26-8
• 化学式: C₆₃H₇₆O₁₄
• 分子量: 1057.29
• InChiKey: RRAIZXIAFASZJR-VKXOEWMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.02
• 重原子数：
  77.0
• 可旋转键数：
  27.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  144.9
• 氢给体数：
  0.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  8-methoxycarbonyloctyl 3-O-benzoyl-4,6-O-cyclohexylidene-2-O-(tetra-O-benzyl-α-D-galactopyranosyl)-α-D-mannopyranoside 在 palladium on activated charcoal 、 sodium methylate 甲醇 、 Rexyn 101 (H+) resin 、 氢气 、 silver trifluoromethanesulfonate 、 1,1,3,3-四甲基脲 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 8-methoxycarbonyloctyl 3-O-(3,6-dideoxy-α-D-arabino-hexopyranosyl)-2-O-α-D-galactopyranosyl-α-D-mannopyranoside
  参考文献：
  名称：

  Antigenic determinants of Salmonella serogroups A and D1.Synthesis of trisaccharide glycosides for use as artificial antigens

  摘要：

  The disaccharide glycoside 8-methoxycarbonyloctyl 4,6-O-cyclohexylidine-2-O-(tetra-O-benzyl-alpha-D-galactopyranosyl)-alpha-D-manno pyranoside (7) was used as a common intermediate to the trisaccharide determinants of both Salmonella serogroups A and D1. Acetalation of 8-methoxycarbonyloctyl alpha-D-mannopyranoside provided the 4,6-acetal derivative, which was selectively benzoylated to give the partially protected mannoside 4. Reaction of 4 with tetra-O-benzyl-alpha-D-galacto-pyranosyl chloride afforded the fully protected disaccharide, which, after transesterification, gave the selectively blocked, disaccharide glycoside (7). Addition of tyvelose by way of its 2,4-di-O-benzoyl-3,6-dideoxy-alpha-D-arabino-hexopyranosyl chloride derivative gave the blocked trisacchride determinant of Salmonella serogroup D1. 2,4,-Di-O-benzyl-3,6-dideoxy-alpha-D-ribo-hexopyranosyl chloride reacted with 7 to provide, after removal of blocking groups, the paratose-containing determinant of serogroup A.

  DOI：

  10.1016/s0008-6215(82)80005-0
• 作为产物：
  描述：

  8-methoxycarbonyloctyl 4,6-O-cyclohexylidene-α-D-mannopyranoside 在 吡啶 、 silver trifluoromethanesulfonate 、 1,1,3,3-四甲基脲 作用下， 以 二氯甲烷 为溶剂， 生成 8-methoxycarbonyloctyl 3-O-benzoyl-4,6-O-cyclohexylidene-2-O-(tetra-O-benzyl-α-D-galactopyranosyl)-α-D-mannopyranoside
  参考文献：
  名称：

  Antigenic determinants of Salmonella serogroups A and D1.Synthesis of trisaccharide glycosides for use as artificial antigens

  摘要：

  The disaccharide glycoside 8-methoxycarbonyloctyl 4,6-O-cyclohexylidine-2-O-(tetra-O-benzyl-alpha-D-galactopyranosyl)-alpha-D-manno pyranoside (7) was used as a common intermediate to the trisaccharide determinants of both Salmonella serogroups A and D1. Acetalation of 8-methoxycarbonyloctyl alpha-D-mannopyranoside provided the 4,6-acetal derivative, which was selectively benzoylated to give the partially protected mannoside 4. Reaction of 4 with tetra-O-benzyl-alpha-D-galacto-pyranosyl chloride afforded the fully protected disaccharide, which, after transesterification, gave the selectively blocked, disaccharide glycoside (7). Addition of tyvelose by way of its 2,4-di-O-benzoyl-3,6-dideoxy-alpha-D-arabino-hexopyranosyl chloride derivative gave the blocked trisacchride determinant of Salmonella serogroup D1. 2,4,-Di-O-benzyl-3,6-dideoxy-alpha-D-ribo-hexopyranosyl chloride reacted with 7 to provide, after removal of blocking groups, the paratose-containing determinant of serogroup A.

  DOI：

  10.1016/s0008-6215(82)80005-0