1,12-anhydro-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-1-(4,6-dibenzyloxy-2-hydroxymethylphenyl)-α-D-arabino-hexopyranose | 131389-39-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1,12-anhydro-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-1-(4,6-dibenzyloxy-2-hydroxymethylphenyl)-α-D-arabino-hexopyranose
• 英文别名: 1,1²-anhydro-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-1-(4,6-dibenzyloxy-2-hydroxymethylphenyl)-α-D-arabino-hexopyranose
• CAS: 131389-39-4
• 化学式: C₄₀H₄₆O₇Si
• 分子量: 666.887
• InChiKey: WHWXYROKPZVNHN-BEMNCASZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.82
• 重原子数：
  48.0
• 可旋转键数：
  9.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  64.61
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  [2-溴-3,5-双(苯甲氧基)苯基]甲醇 、 1,5-anhydro-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-1-tributylstannyl-D-arabino-hex-1-enitol 在 四(三苯基膦)钯 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以15%的产率得到1,1'-bis(1,5-anhydro-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-D-arabino-hex-1-enitol)
  参考文献：
  名称：

  Papulacandins and chaetiacandin: a stereoselective route to their basic skeleton by a palladium-mediated arylation of 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-1-tributylstannyl-d-glucal

  摘要：

  Palladium(0)-catalysed coupling of 1,5-anhydro-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-1-tributylstannyl-D-arabino-hex-1-enitol (7) with 3,5-dibenzyloxy-2-bromobenzyl alcohol gave 1,1(2)-anhydro-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-1-(4,6-dibenzyloxy-2-hydroxymethyl-phenyl-alpha-D-arabino-hexopyranose (13). The same reaction buffered by sodium carbonate provided 1,5-anhydro-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-1-(4,6-dibenzyloxy-2-hydroxymethyl-phenyl)-D-arabino-hex-1-enitol (11). Stereoselective oxidative spiroacetalisation of 11 provided 1,(2)-anhydro-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-1-(4,6-dibenzyloxy-2-hydroxymethyl-phenyl)-alpha-D-glucopyranose (15), the basic tricyclic structure of papulacandins. In a model study, 15 was converted in three steps into 1,1(2)-anhydro-1-(4,6-dihydroxy-2-hydroxymethylphenyl)-3-O-octadecanoyl-alpha-D-glucopyranose (24), a structural analogue of papulacandin D. Moreover, stereoselective hydroboration-oxidation of 11 furnished 2-(4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-beta-D-glucopyranosyl)-3,5-dibenzyloxy-1-hydroxymethylbenzene (26), the structural skeleton of the chaetiacandin 3.

  DOI：

  10.1016/0008-6215(92)80014-r

文献信息

• Arylation of 1-tributylstannyl glycals catalyzed by palladium: A synthetic route to the basic skeleton of the papulacandins and chaetiacandin
  作者：Eric Dubois、Jean-Marie Beau

  DOI：10.1016/s0040-4039(00)97832-8

  日期：1990.1