methyl 2,3,6-tri-O-benzyl-β-D-mannopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-mannopyranoside | 1225486-36-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2,3,6-tri-O-benzyl-β-D-mannopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-mannopyranoside
• 英文别名: Bn(-2)[Bn(-3)][Bn(-6)]Man(b1-4)[Bn(-2)][Bn(-3)][Bn(-6)]a-Man1Me；(2R,3R,4S,5S,6S)-6-[(2R,3R,4S,5S,6S)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-yl]oxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-ol
• CAS: 1225486-36-1
• 化学式: C₅₅H₆₀O₁₁
• 分子量: 897.075
• InChiKey: AOHOBOWOJXBEMI-ZVZZRAMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  66
• 可旋转键数：
  23
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 、 methyl 2,3,6-tri-O-benzyl-β-D-mannopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-mannopyranoside 在 1-(苯基亚硫酰基)哌啶 、 三氟甲磺酸酐 、 2,4,6-三叔丁基嘧啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以70%的产率得到methyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-3-O-acetyl-6-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-benzyl-β-D-mannopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Convergent synthesis of the tetrasaccharide repeating unit related to the O-antigenic polysaccharide of Escherichia coli 78

  摘要：

  A convergent synthesis of the tetrasaccharide repeating unit of the O-antigenic cell wall polysaccharide of Escherichia coli 78, as the corresponding methyl glycoside (I), is being reported. It involved stereoselective glycosidation of a beta-linked mannodisaccharide acceptor with a beta-linked glucosamine based disaccharide thioglycoside donor, which were prepared from the corresponding functionalised monosaccharide based glycosyl donors and acceptors. The resulting tetrasaccharide derivative was finally converted to (I) by selective deprotection and also by global protection and deprotection techniques. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.02.052
• 作为产物：
  描述：

  (2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1->4)-1-O-methyl-2,3,6-tri-O-benzyl-α-D-glucopyranose 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 生成 、 methyl 2,3,6-tri-O-benzyl-β-D-mannopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Convergent synthesis of the tetrasaccharide repeating unit related to the O-antigenic polysaccharide of Escherichia coli 78

  摘要：

  A convergent synthesis of the tetrasaccharide repeating unit of the O-antigenic cell wall polysaccharide of Escherichia coli 78, as the corresponding methyl glycoside (I), is being reported. It involved stereoselective glycosidation of a beta-linked mannodisaccharide acceptor with a beta-linked glucosamine based disaccharide thioglycoside donor, which were prepared from the corresponding functionalised monosaccharide based glycosyl donors and acceptors. The resulting tetrasaccharide derivative was finally converted to (I) by selective deprotection and also by global protection and deprotection techniques. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.02.052

文献信息

• Convergent synthesis of the tetrasaccharide repeating unit related to the O-antigenic polysaccharide of Escherichia coli 78
  作者：Sajal K. Maity、Amarendra Patra、Rina Ghosh

  DOI：10.1016/j.tet.2010.02.052

  日期：2010.4

  A convergent synthesis of the tetrasaccharide repeating unit of the O-antigenic cell wall polysaccharide of Escherichia coli 78, as the corresponding methyl glycoside (I), is being reported. It involved stereoselective glycosidation of a beta-linked mannodisaccharide acceptor with a beta-linked glucosamine based disaccharide thioglycoside donor, which were prepared from the corresponding functionalised monosaccharide based glycosyl donors and acceptors. The resulting tetrasaccharide derivative was finally converted to (I) by selective deprotection and also by global protection and deprotection techniques. (C) 2010 Elsevier Ltd. All rights reserved.