(2S,3R,4S,5E,8R,9S,10S,11R,12R,13R)-3-(3,4-Dimethoxybenzyloxy)-12-<(1,1-dimethylethyl)dimethylsilyloxy>-1-<(1,1-dimethylethyl)diphenylsilyloxy>-13-(4-methoxybenzyloxy)-2,4,8,10,12-pentamethyl-9,11-(2,4,6-trimethylbenzylidenedioxy)pentadec-5-ene | 124602-69-3

• 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: (2S,3R,4S,5E,8R,9S,10S,11R,12R,13R)-3-(3,4-Dimethoxybenzyloxy)-12-<(1,1-dimethylethyl)dimethylsilyloxy>-1-<(1,1-dimethylethyl)diphenylsilyloxy>-13-(4-methoxybenzyloxy)-2,4,8,10,12-pentamethyl-9,11-(2,4,6-trimethylbenzylidenedioxy)pentadec-5-ene
• CAS: 124602-69-3
• 化学式: C₆₉H₁₀₀O₉Si₂
• 分子量: 1129.72
• InChiKey: FHTQXIJPEZXTGA-NXTGDBLBSA-N

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S,5E,8R,9S,10S,11R,12R,13R)-3-(3,4-Dimethoxybenzyloxy)-12-<(1,1-dimethylethyl)dimethylsilyloxy>-1-<(1,1-dimethylethyl)diphenylsilyloxy>-13-(4-methoxybenzyloxy)-2,4,8,10,12-pentamethyl-9,11-(2,4,6-trimethylbenzylidenedioxy)pentadec-5-ene 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 丙酮 为溶剂， 反应 48.0h， 以33%的产率得到(2S,3R,4S,5R,6R,8R,9S,10S,11R,12R,13R)-3-(3,4-Dimethoxybenzyloxy)-12-<(1,1-dimethylethyl)dimethylsilyloxy>-1-<(1,1-dimethylethyl)diphenylsilyloxy>-13-(4-methoxybenzyloxy)-2,4,8,10,12-pentamethyl-9,11-(2,4,6-trimethylbenzylidenedioxy)pentadecane-5,6-diol
  参考文献：
  名称：

  Stereoselective synthesis of erythronolide a by extremely efficient lactonization based on conformational adjustment and high activation of seco-acid1

  摘要：

  C1-C5 sulfone (11) and C7-C15 aldehyde (20), synthesized stereoselectively from D-glucose, were coupled, and the C5 and C6 chiral centers were constructed taking advantage of the MPM (4-methoxybenzyl) type protecting group to give the seco-acid (7), which has 9,11- and 3,5-diols protected as the mesityl- and DMP (3,4-dimethoxyphenyl) acetals, respectively. When Yamaguchi''s mixed anhydride of 7 was treated with a high concentration of DMAP at room temperature, a very rapid cyclization occurred and the 14-membered lactone (8) was isolated in almost quantitative yield. Deprotection of 8 readily gave 9-dihydroerythronolide A (2), which was converted to the title compound (1).

  DOI：

  10.1016/s0040-4020(01)85585-x
• 作为产物：
  描述：

  在 amalgan 、 sodium 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 5.0h， 以82%的产率得到(2S,3R,4S,5E,8R,9S,10S,11R,12R,13R)-3-(3,4-Dimethoxybenzyloxy)-12-<(1,1-dimethylethyl)dimethylsilyloxy>-1-<(1,1-dimethylethyl)diphenylsilyloxy>-13-(4-methoxybenzyloxy)-2,4,8,10,12-pentamethyl-9,11-(2,4,6-trimethylbenzylidenedioxy)pentadec-5-ene
  参考文献：
  名称：

  Stereoselective synthesis of erythronolide a by extremely efficient lactonization based on conformational adjustment and high activation of seco-acid1

  摘要：

  C1-C5 sulfone (11) and C7-C15 aldehyde (20), synthesized stereoselectively from D-glucose, were coupled, and the C5 and C6 chiral centers were constructed taking advantage of the MPM (4-methoxybenzyl) type protecting group to give the seco-acid (7), which has 9,11- and 3,5-diols protected as the mesityl- and DMP (3,4-dimethoxyphenyl) acetals, respectively. When Yamaguchi''s mixed anhydride of 7 was treated with a high concentration of DMAP at room temperature, a very rapid cyclization occurred and the 14-membered lactone (8) was isolated in almost quantitative yield. Deprotection of 8 readily gave 9-dihydroerythronolide A (2), which was converted to the title compound (1).

  DOI：

  10.1016/s0040-4020(01)85585-x