O-(2,3,4,6-Tetra-O-benzoyl-β-D-glucopyranosyl)-(1->6)-O-(2,3,4-tri-O-benzoyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-α-D-galactopyranosyl chloride | 143249-63-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: O-(2,3,4,6-Tetra-O-benzoyl-β-D-glucopyranosyl)-(1->6)-O-(2,3,4-tri-O-benzoyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-α-D-galactopyranosyl chloride
• CAS: 143249-63-2
• 化学式: C₈₈H₇₁ClO₂₅
• 分子量: 1563.97
• InChiKey: VGADVEXICPOCRY-AVNMEKLQSA-N

反应信息

• 作为产物：
  描述：

  O-(2,3,4,6-Tetra-O-benzoyl-β-D-glucopyranosyl)-(1->6)-O-(2,3,4-tri-O-benzoyl-β-D-glucopyranosyl)-(1->6)-1,2,3,4-tetra-O-benzoyl-α-D-galactopyranose 在 zinc(II) chloride 作用下， 以 氯仿 为溶剂， 反应 3.0h， 以78%的产率得到O-(2,3,4,6-Tetra-O-benzoyl-β-D-glucopyranosyl)-(1->6)-O-(2,3,4-tri-O-benzoyl-β-D-glucopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-α-D-galactopyranosyl chloride
  参考文献：
  名称：

  Binding studies on internal immunodeterminants: synthesis of β-(1 → 6)-linked oligosaccharide methyl glycosides having one to four internal d-galactopyranosyl residues flanked by gentiobiose residues

  摘要：

  The oligosaccharide glycosides beta-D-Glc p-(1 --> 6)-beta-D-Glc p-(1 --> 6)-[beta-D-Gal p-(1 --> 6)]n-beta-D-Glc p-(1 --> 6)-beta-D-Glc p-1 --> OMe (n = 1-4) were prepared by a convergent block synthesis. Haloacetyl, tert-butyldiphenylsilyl, and dimethylthexylsilyl groups were used as temporary protective groups for the preparation of the intermediate glycosyl donors and acceptors. The deoxygenated trisaccharide glyco-sides beta-D-Glc p-(1 --> 6)-beta-D-Gal p-(1 --> 6)-4-deoxy-beta-D-xylo-Hex p-1 --> OMe and beta-D-Glc p-(1 --> 6)-4-deoxy-beta-D-xylo-Hex p-(1 --> 6)-beta-D-Gal p-1 --> OMe were also synthesized. The binding of each glycoside to the monoclonal antigalactan antibody IgA 1539 was studied and the results support the previous finding that J539 can bind to internal antigenic epitopes. The data are consistent with the interpretation that subsite C of that antibody binds glucose with a K(a) of approximately 6 (cf. 10.9 for galactose).

  DOI：

  10.1016/s0008-6215(00)90575-5