1-acetoxymethyl-3,5-dibenzyloxy-2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)benzene | 131389-46-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-acetoxymethyl-3,5-dibenzyloxy-2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)benzene
• 英文别名: [(2R,3R,4R,5S,6S)-3,4,5-triacetyloxy-6-[2-(acetyloxymethyl)-4,6-bis(phenylmethoxy)phenyl]oxan-2-yl]methyl acetate
• CAS: 131389-46-3
• 化学式: C₃₇H₄₀O₁₃
• 分子量: 692.717
• InChiKey: VRMXRRBNYBPFSV-JMUSVNSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  50
• 可旋转键数：
  19
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  159
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  乙酸酐 、 2-(4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-β-D-glucopyranosyl)-3,5-dibenzyloxy-1-hydroxymethylbenzene 在 吡啶 、 盐酸 作用下， 生成 1-acetoxymethyl-3,5-dibenzyloxy-2-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)benzene
  参考文献：
  名称：

  Arylation of 1-tributylstannyl glycals catalyzed by palladium: A synthetic route to the basic skeleton of the papulacandins and chaetiacandin

  摘要：

  DOI：

  10.1016/s0040-4039(00)97832-8

文献信息

• 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
  作者：Eric Dubois、Jean-Marie Beau

  DOI：10.1016/0008-6215(92)80014-r

  日期：1992.1

  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.
• DUBOIS, E.;BEAU, J. -M., TETRAHEDRON LETT., 31,(1990) N6, C. 5165-5168
  作者：DUBOIS, E.、BEAU, J. -M.

  DOI：——

  日期：——