methyl 2,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside | 904300-25-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside
• CAS: 904300-25-0
• 化学式: C₅₅H₆₀O₁₁
• 分子量: 897.075
• InChiKey: LZIHJBDYWVJUMI-FCYBBGCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.6
• 重原子数：
  66.0
• 可旋转键数：
  23.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  112.53
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  methyl 2,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside 、 3,4,6-tri-O-acetyl-2-bromo-2-deoxy-α-D-mannopyramnosyl bromide 在 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 12.0h， 以81%的产率得到methyl 3,4,6-tri-O-acetyl-2-bromo-2-deoxy-α-D-mannopyranosyl-(1→3)-2,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1→2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  三糖α-d-Glcp-（1→3）-α-d-Manp-（1→2）-α的四个（4''-，2''-，2'-和6-）单脱氧类似物的合成-d-ManpOMe被钙网蛋白/钙连接蛋白识别

  摘要：

  有效合成三糖α-D-Glcp-（1→3）-α-D-Manp-（1→2）的四个（4“-，2”-，2'-和6-）单脱氧类似物的途径）-α-D-ManpOMe已开发。对于引入2'-和2“-脱氧基序，最有效的方法是在三氟甲磺酸银促进的偶联中使用1,2-二溴-甘露糖基供体来构建α-糖苷键，然后还原在二糖或三糖水平上将2-溴官能转变为2-脱氧基序。相反，在单糖阶段已经引入了4”-和6-脱氧功能。合成中最具挑战性的部分是非还原性顺式-α-D-糖苷键的立体选择性形成。

  DOI：

  10.1016/j.carres.2015.07.006
• 作为产物：
  描述：

  methyl 3,4,6-tri-O-benzyl-α-D-mannopyranoside 在 N-碘代丁二酰亚胺 、 4 A molecular sieve 、 sodium methylate 、 silver trifluoromethanesulfonate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 72.5h， 生成 methyl 2,4,6-tri-O-benzyl-α-D-mannopyranosyl-(1->2)-3,4,6-tri-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of monodeoxy analogues of the trisaccharide α-d-Glcp-(1→3)-α-d-Manp-(1→2)-α-d-ManpOMe recognised by Calreticulin/Calnexin

  摘要：

  Six (3,4,4',6',3" or 6")-monodeoxy analogues of the title trisaccharide (1-6) have been prepared utilising monodeoxy monosaccharide precursors. The reducing end deoxy derivatives were synthesised by N-iodosuccinimide/silver trifluoromethanesulfonate (NIS/AgOTf)-promoted couplings of a common disaccharide thioglycoside donor 10 to suitably protected monodeoxy acceptors 9 and 12, affording trisaccharides, which after deprotection yielded target structures 1 and 2. The non-reducing end deoxy derivatives could similarly be produced by halide-assisted glycosylations of a common disaccharide acceptor 17 with monodeoxy glycosyl bromide donors (obtained from thioglycosides 18 and 20) to yield, after removal of protecting groups, target trisaccharides 3 and 4. The analogues with the deoxy function in the middle mannose residue, were obtained through orthogonal halide-assisted coupling of tetrabenzyl-glucopyranosyl bromide to monodeoxy thioglycoside acceptors to give thioglycoside disaccharides, which subsequently were used as donors in NIS/AgOTf-promoted couplings to a common 2-hydroxy-mannose acceptor 15 to afford trisaccharides; deprotection yielded the final target compounds 5 and 6. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.03.015