Acetic acid 4-((2R,4R,5R,6R)-4,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5-methoxy-8-oxo-bicyclo[4.2.0]octa-1(6),2,4-trien-7-yl ester | 314280-51-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: Acetic acid 4-((2R,4R,5R,6R)-4,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5-methoxy-8-oxo-bicyclo[4.2.0]octa-1(6),2,4-trien-7-yl ester
• 英文别名: [5-methoxy-4-[(2R,4R,5R,6R)-6-methyl-4,5-bis(phenylmethoxy)oxan-2-yl]-8-oxo-7-bicyclo[4.2.0]octa-1(6),2,4-trienyl] acetate
• CAS: 314280-51-8
• 化学式: C₃₁H₃₂O₇
• 分子量: 516.591
• InChiKey: ORVUKNYDJLTOTL-MBWSBRMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  80.3
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Acetic acid 4-((2R,4R,5R,6R)-4,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5-methoxy-8-oxo-bicyclo[4.2.0]octa-1(6),2,4-trien-7-yl ester 在 disodium hydrogenphosphate 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以95%的产率得到Acetic acid 6-((2R,4R,5R,6R)-4,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-7-methoxy-3-oxo-1,3-dihydro-isobenzofuran-1-yl ester
  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)-5,8,8-trimethoxy-bicyclo[4.2.0]octa-1(6),2,4-trien-7-one 在 甲醇 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 2.5h， 生成 Acetic acid 4-((2R,4R,5R,6R)-4,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-5-methoxy-8-oxo-bicyclo[4.2.0]octa-1(6),2,4-trien-7-yl ester
  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