octyl 3,4,6-tri-O-benzyl-2-O-(methylthio)thiocarbonyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-mannopyranoside | 849465-35-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: octyl 3,4,6-tri-O-benzyl-2-O-(methylthio)thiocarbonyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-mannopyranoside
• CAS: 849465-35-6
• 化学式: C₆₄H₇₆O₁₁S₂
• 分子量: 1085.43
• InChiKey: KPCNKUPYRLFYDR-BBUUEFPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.01
• 重原子数：
  77.0
• 可旋转键数：
  31.0
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  101.53
• 氢给体数：
  0.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  octyl 3,4,6-tri-O-benzyl-2-O-(methylthio)thiocarbonyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-mannopyranoside 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以61%的产率得到octyl 3,4,6-tri-O-benzyl-2-deoxy-α-D-arabino-hexopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Modified mannose disaccharides as substrates and inhibitors of a polyprenol monophosphomannose-dependent α-(1→6)-mannosyltransferase involved in mycobacterial lipoarabinomannan biosynthesis

  摘要：

  A panel of alpha-(1 6)-linked mannose disaccharides (5-8) in which the 2'-OH group has been replaced, independently, by deoxy, fluoro, amino, and methoxy functionalities has been synthesized. Evaluation of these compounds as potential substrates or inhibitors of a polyprenol monophosphomannose-dependent alpha-(1-6)-mannosyltransferase involved in mycobacterial LAM biosynthesis demonstrated that the enzyme is somewhat tolerant substitution at this site. The enzyme recognizes the disaccharides with groups similar or smaller in size than the native hydroxyl (6-8), but not the disaccharide with the more sterically demanding methoxy group (5). The 2'-OH appears not form a critical hydrogen bonding interaction with the protein as the 2'-deoxy analog is a substrate for the enzyme. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.11.027
• 作为产物：
  描述：

  octyl α-D-mannopyranoside 在 吡啶 、 咪唑 、 N-碘代丁二酰亚胺 、 sodium methylate 、 silver trifluoromethanesulfonate 、 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.75h， 生成 octyl 3,4,6-tri-O-benzyl-2-O-(methylthio)thiocarbonyl-α-D-mannopyranosyl-(1->6)-2,3,4-tri-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  Modified mannose disaccharides as substrates and inhibitors of a polyprenol monophosphomannose-dependent α-(1→6)-mannosyltransferase involved in mycobacterial lipoarabinomannan biosynthesis

  摘要：

  A panel of alpha-(1 6)-linked mannose disaccharides (5-8) in which the 2'-OH group has been replaced, independently, by deoxy, fluoro, amino, and methoxy functionalities has been synthesized. Evaluation of these compounds as potential substrates or inhibitors of a polyprenol monophosphomannose-dependent alpha-(1-6)-mannosyltransferase involved in mycobacterial LAM biosynthesis demonstrated that the enzyme is somewhat tolerant substitution at this site. The enzyme recognizes the disaccharides with groups similar or smaller in size than the native hydroxyl (6-8), but not the disaccharide with the more sterically demanding methoxy group (5). The 2'-OH appears not form a critical hydrogen bonding interaction with the protein as the 2'-deoxy analog is a substrate for the enzyme. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.11.027