methyl O-(2,3,4-tri-O-benzoyl-β-D-galactopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside | 101802-83-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl O-(2,3,4-tri-O-benzoyl-β-D-galactopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside
• 英文别名: [(2R,3S,4S,5R,6R)-4,5-dibenzoyloxy-2-(hydroxymethyl)-6-[[(2R,3S,4S,5R,6R)-3,4,5-tribenzoyloxy-6-methoxyoxan-2-yl]methoxy]oxan-3-yl] benzoate
• CAS: 101802-83-9
• 化学式: C₅₅H₄₈O₁₇
• 分子量: 980.976
• InChiKey: HOYSEHMWEWWLCF-XSHFDICZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.45
• 重原子数：
  72.0
• 可旋转键数：
  17.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  214.95
• 氢给体数：
  1.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  2,3-di-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-4-deoxy-α-D-xylo-hexopyranosyl chloride 、 methyl O-(2,3,4-tri-O-benzoyl-β-D-galactopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside 在 2,4,6-三甲基吡啶 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以93%的产率得到methyl O-<2,3-di-O-benzoyl-6-O-(tert-butyldiphenylsilyl)-4-deoxy-β-D-xylo-hexopyranosyl>-(1->6)-O-(2,3,4-tri-O-benzoyl-β-D-galactopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of specifically deoxygenated ligands related to (1→6)-β-d-galacto-oligosaccharides, and studies on their binding to monoclonal antigalactan antibodies

  摘要：

  Synthetic deoxygenated derivatives of methyl beta-glycosides of (1----6)-beta-D-galacto-oligosaccharides were prepared, and their binding to antigalactan monoclonal antibodies X24 and J539 (Fab') was studied. The results suggest the involvement of an additional, critical hydrogen bond in the highest affinity subsite (A), which now appears to require two hydrogen bonds from the 2- and 3-hydroxyls of the galactosyl residue to the protein, and one from the protein to O-4 of that residue. The data obtained with a series of oligosaccharides deoxygenated at position 3(1), 3(2), 3(3), 4(1), 4(2), or 4(3) support the binding patterns and subsite-arrangement inferred previously from studies with large numbers of deoxyfluoro-substituted ligands and this family of antibodies.

  DOI：

  10.1016/0008-6215(90)84033-q
• 作为产物：
  描述：

  methyl 2,3,4-tri-O-benzoyl-6-O-bromoacetyl-β-D-galactopyranoside 在 2,4,6-三甲基吡啶 、 1,1-二氯甲醚 、 silver trifluoromethanesulfonate 、 硫脲 、 zinc(II) chloride 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 0.75h， 生成 methyl O-(2,3,4-tri-O-benzoyl-β-D-galactopyranosyl)-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside
  参考文献：
  名称：

  通过逐步和嵌段方法高效化学合成β-（1→6）-连接的d-半乳糖寡糖的甲基β-糖苷

  摘要：

  甲基2,3,4-三-O-苯甲酰基-β-D-吡喃半乳糖苷（1）的溴乙酰化反应，然后用1,1-二氯甲基甲基醚将生成的6-O-溴乙酰基衍生物2的甲氧基裂解，3，4-三-O-苯甲酰基-6-O-溴乙酰基-α-D-吡喃半乳糖基氯（3）。三氟甲磺酸银促进3与1的反应，得到甲基O-（2,3,4-三-O-苯甲酰基-6-O-溴乙酰基-β-D-吡喃半乳糖基）-（1 ---- 6）- 2,3,4-三-O-苯甲酰基-β-D-吡喃半乳糖苷（12），在其非还原端基的O-6处带有可选择性除去的溴乙酰基。将其O-脱溴乙酰化，并将形成的二糖亲核试剂15再次用3处理，得到类似的三糖18。重复该反应序列，得到类似的四糖20，显示了逐步构建标题寡糖的可行性。3与1,2,3,4-四-O-苯甲酰基-α-（7）和β-D-吡喃半乳糖（5）的相似反应分别得到O-（2,3,4-tri-O-苯甲酰基-6-O-溴乙酰基-β-D-吡喃半乳糖基）-（1

  DOI：

  10.1016/s0008-6215(00)90266-0

文献信息

• A synthetic heptasaccharide reveals the capability of a monoclonal antibody to read internal epitopes of a polysaccharide antigen
  作者：Thomas Ziegler、Pavol Kováč、Cornelis P.J. Glaudemans

  DOI：10.1016/0008-6215(90)80022-u

  日期：1990.8

  all-beta-(1----6)-linked methyl galactotetraoside 13, having O-6(4) free, followed by debenzoylation of the formed, fully protected methyl galactoheptaoside. The blockwise synthesis of the nucleophile 13 from readily available monosaccharides, and the synthesis of 5 from the corresponding beta-1-O-benzoylated trisaccharide, is also described. Heptasaccharide 10 binds with the (1----6)-beta-D-galactan-specific monoclonal

  合成七糖，β-D-Galp-（1 ---- 3）-β-D-Galp-（1 ---- 6）-β-D-Galp-（1 ---- 6的结合β-D-Galp-（1 ---- 6）-β-D-Galp-1-OCH3（10）与X24基因家族的两个单克隆IgAs进行了研究。通过三氟甲磺酸银介导的O-（2,3,4,6-四-O-苯甲酰基-β-D-吡喃半乳糖基）-（1-3）-O-（2,4）的偶联合成配体10 ，6，-t-ri-O-苯甲酰基-β-D-吡喃半乳糖基）-（1 ---- 3）-2,4,6-三-O-苯甲酰基-α-D-吡喃半乳糖基氯（5）苯甲酰化的，全β-（1–6）连接的甲基半乳糖四糖苷13，不含O-6（4），然后对形成的，完全保护的甲基半乳糖庚糖苷进行脱苯甲酰化。还描述了由容易获得的单糖的亲核试剂13的嵌段合成，以及由相应的β-1-O-苯甲酰化三糖的5的合成。七糖10与（1 ---- 6）-β-D-半乳聚
• Synthesis of a series of methyl β-glycosides of (1→6)-β-d-galacto-oligosaccharides having one residue deoxygenated at position 3
  作者：Pavol Kováč、Kevin J. Edgar

  DOI：10.1016/0008-6215(90)84226-k

  日期：1990.6

  Methyl beta-glycosides of beta-(1----6)-linked D-galactobioses (13 and 16) and -galactotrioses (21, 24, and 26) containing a 3-deoxy-beta-D-xylo-hexopyranosyl moiety either as one of the end units or the internal unit have been synthesized. The extension of the oligosaccharide chain was achieved, inter alia, by the use of two newly synthesized glycosyl donors derived from 3-deoxy-D-xylo-hexopyranose, namely, 2,4,6-tri-O-benzoyl-3-deoxy-a-D-xylo-hexopyranosyl chloride (8) and 2,4-di-O-benzoyl-6-O-bromoacetyl-3-deoxy-a-D-xylo-hexopyranosyl chloride (10). Glycosylation reactions were mediated by silver triflate under base-deficient conditions.
• ZIEGLER, THOMAS;KOVAC, PAVOL;GLAUDEMANS, CORNELIS P. J., CARBOHYDR. RES., 203,(1990) N, C. 253-263
  作者：ZIEGLER, THOMAS、KOVAC, PAVOL、GLAUDEMANS, CORNELIS P. J.

  DOI：——

  日期：——
• KOVAC, PAVOL;EDGAR, KEVIN J., CARBOHYDR. RES., 201,(1990) N, C. 79-93
  作者：KOVAC, PAVOL、EDGAR, KEVIN J.

  DOI：——

  日期：——
• Systematic chemical synthesis of (1→6)-β-d-galacto-oligosaccharides and related compounds
  作者：Pavol Kováč

  DOI：10.1016/s0008-6215(00)90686-4

  日期：1985.12