3,5-O-(3,4-Dimethoxybenzylidene)-13-O-(4-methoxybenzyl)-9,11-O-(2,4,6-trimethylbenzylidene)-(9S)-9-dihydroerythronolide A seco-acid methylester | 131755-85-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 3,5-O-(3,4-Dimethoxybenzylidene)-13-O-(4-methoxybenzyl)-9,11-O-(2,4,6-trimethylbenzylidene)-(9S)-9-dihydroerythronolide A seco-acid methylester
• CAS: 131755-85-6
• 化学式: C₄₉H₇₀O₁₂
• 分子量: 851.088
• InChiKey: LTHIFYORGSLIEA-AFHLLEHSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.51
• 重原子数：
  61.0
• 可旋转键数：
  17.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  140.6
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  3,5-O-(3,4-Dimethoxybenzylidene)-13-O-(4-methoxybenzyl)-9,11-O-(2,4,6-trimethylbenzylidene)-(9S)-9-dihydroerythronolide A seco-acid methylester 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 0.33h， 以80%的产率得到3,5-O-(3,4-Dimethoxybenzylidene)-9,11-O-(2,4,6-trimethylbenzylidene)-(9S)-9-dihydroerythronolide A seco-acid methylester
  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：

  (3R)-3-[(2R,4S,5S,6R)-6-[(2R,3R)-2-[tert-butyl(dimethyl)silyl]oxy-3-[(4-methoxyphenyl)methoxy]pentan-2-yl]-5-methyl-2-(2,4,6-trimethylphenyl)-1,3-dioxan-4-yl]-1-[(2R,5S,6R)-6-[(2S)-1-[tert-butyl(diphenyl)silyl]oxypropan-2-yl]-2-(3,4-dimethoxyphenyl)-5-methyl-1,3-dioxan-4-yl]butan-1-ol 在 jones reagent 、 草酰氯 、 四丁基氟化铵 、 potassium carbonate 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 乙醚 为溶剂， 反应 53.8h， 生成 3,5-O-(3,4-Dimethoxybenzylidene)-13-O-(4-methoxybenzyl)-9,11-O-(2,4,6-trimethylbenzylidene)-(9S)-9-dihydroerythronolide A seco-acid methylester
  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