4-((2R,4R,5R,6R)-4,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5,8,8-trimethoxy-bicyclo[4.2.0]octa-1(6),2,4-trien-7-one | 314280-49-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-((2R,4R,5R,6R)-4,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5,8,8-trimethoxy-bicyclo[4.2.0]octa-1(6),2,4-trien-7-one
• 英文别名: 5,8,8-trimethoxy-4-[(2R,4R,5R,6R)-6-methyl-4,5-bis(phenylmethoxy)oxan-2-yl]bicyclo[4.2.0]octa-1(6),2,4-trien-7-one
• CAS: 314280-49-4
• 化学式: C₃₁H₃₄O₇
• 分子量: 518.607
• InChiKey: OPPICBKQIPYXLB-NEUGJCOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-((2R,4R,5R,6R)-4,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5,8,8-trimethoxy-bicyclo[4.2.0]octa-1(6),2,4-trien-7-one 在 咪唑 、 甲醇 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.75h， 生成 3-((2R,4R,5R,6R)-4,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-8-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-bicyclo[4.2.0]octa-1(6),2,4-trien-7-one
  参考文献：
  名称：

  Synthetic study of aquayamycin. Part 1: Synthesis of 3-(phenylsulfonyl)phthalides possessing a β-C-olivoside

  摘要：

  An efficient synthetic route to 3-(phenylsulfonyl)phthalides possessing a beta -C-olivoside was developed by exploiting the regioselective [2+2] cycloaddition of benzyne with ketene silyl acetal. The compounds are useful in the total synthesis of the angucyclines, including aquayamycin. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01478-7
• 作为产物：
  描述：

  [4-((2R,4R,5R,6R)-4,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5,7,8,8-tetramethoxy-bicyclo[4.2.0]octa-1(6),2,4-trien-7-yloxy]-trimethyl-silane 在 potassium fluoride 、 四丁基氯化铵 作用下， 以 乙腈 为溶剂， 反应 0.67h， 生成 4-((2R,4R,5R,6R)-4,5-Bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5,8,8-trimethoxy-bicyclo[4.2.0]octa-1(6),2,4-trien-7-one
  参考文献：
  名称：

  Synthetic study of aquayamycin. Part 1: Synthesis of 3-(phenylsulfonyl)phthalides possessing a β-C-olivoside

  摘要：

  An efficient synthetic route to 3-(phenylsulfonyl)phthalides possessing a beta -C-olivoside was developed by exploiting the regioselective [2+2] cycloaddition of benzyne with ketene silyl acetal. The compounds are useful in the total synthesis of the angucyclines, including aquayamycin. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01478-7