8-methoxycarbonyloctyl 4,6-O-cyclohexylidene-2-O-(tetra-O-benzyl-α-D-galactopyranosyl)-α-D-mannopyranoside | 82086-27-9

• 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 4,6-O-cyclohexylidene-2-O-(tetra-O-benzyl-α-D-galactopyranosyl)-α-D-mannopyranoside
• CAS: 82086-27-9
• 化学式: C₅₆H₇₂O₁₃
• 分子量: 953.18
• InChiKey: OWACYNUUIVHDAK-NLVIQCCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.15
• 重原子数：
  69.0
• 可旋转键数：
  25.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  138.83
• 氢给体数：
  1.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  8-methoxycarbonyloctyl 4,6-O-cyclohexylidene-2-O-(tetra-O-benzyl-α-D-galactopyranosyl)-α-D-mannopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 为溶剂， 以93%的产率得到8-methoxycarbonyloctyl 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：

  (2R,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-chloro-tetrahydro-pyran 在 sodium methylate 甲醇 、 Rexyn 101 (H+) resin 、 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 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

文献信息

• Antigenic determinant of Salmonella serogroup B. Synthesis of a trisaccharide glycoside for use as an artificial antigen
  作者：B.Mario Pinto、David R. Bundle

  DOI：10.1016/0008-6215(84)85211-8

  日期：1984.10

  anticipated’ that this trisaccharide sequence, namely, a-D-Gal-(1+2)-[3,6-dideoxy-cu-Dhexopyranosyl-(1+3)]-cy_D-M an, would be related to the dominant role played by the 3,6-dideoxyhexoses in Salmonella serology, owing to the considerable conformational rigidity imposed by the pyranosyl substituents at vicinal oxygen atoms (O-2 and O-3)9Jo. We now report the synthesis of the branched trisaccharide structure corresponding

  已经投入了大量的努力来合成与沙门氏菌血清群A，B和D的O-抗原有关的抗原决定簇。迄今为止，在O特异性链的二糖和高阶线性低聚糖半抗原的合成中出现了一些报告V。另外，我们最近报道了沙门氏菌血清群A和D的两支三糖半抗原的合成，这些半抗原适当地衍生化以允许共价结合到蛋白质，细胞表面和免疫吸收支持物上。可以预期，该三糖序列，即aD-Gal-（1 + 2）-[3,6-二脱氧-cu-Dhexopyranosyl-（1 + 3）]-cy_D-M an将与显性3,6-二脱氧己糖在沙门氏菌血清学中的作用，由于吡喃糖基取代基在邻位氧原子（O-2和O-3）9Jo处具有相当高的构象刚度。现在，我们报告了与沙门氏菌血清群B的0抗原决定簇相对应的支链三糖结构的合成。此研究程序中合成的化合物很有意义，因为它们可用于推断O抗原构象9Jo的模型，协助从体细胞融合实验中选择杂交骨髓瘤抗体”，并研究沙门氏菌抗原与单克隆抗体的相互