(2R,3S,4R,5R,6R)-5-Benzyloxy-2-ethylsulfanyl-6-methyl-4-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-ol | 904300-37-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,3S,4R,5R,6R)-5-Benzyloxy-2-ethylsulfanyl-6-methyl-4-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-ol
• CAS: 904300-37-4
• 化学式: C₄₉H₅₆O₉S
• 分子量: 821.044
• InChiKey: OCANQLBSLFNFDR-QFIFULKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.51
• 重原子数：
  59.0
• 可旋转键数：
  20.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  94.07
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R,5R,6R)-5-Benzyloxy-2-ethylsulfanyl-6-methyl-4-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-ol 在 N-碘代丁二酰亚胺 、 4 A molecular sieve 、 silver trifluoromethanesulfonate 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 26.5h， 生成 methyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-D-rhamnopyranosyl-(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
• 作为产物：
  描述：

  乙基beta-硫代吡喃葡萄糖苷四苄基 在 4 A molecular sieve 、 四乙基溴化铵 、 溴 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 41.0h， 生成 (2R,3S,4R,5R,6R)-5-Benzyloxy-2-ethylsulfanyl-6-methyl-4-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-ol
  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