(2R,3S,4S,5R,6R,7R)-1-Benzoyloxy-6-<(1,1-dimethylethyl)dimethylsilyloxy>-7-(4-methoxybenzyloxy)-2,4,6-trimethyl-3,5-(2,4,6-trimethylbenzylidenedioxy)nonanal | 131755-79-8

• 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: (2R,3S,4S,5R,6R,7R)-1-Benzoyloxy-6-<(1,1-dimethylethyl)dimethylsilyloxy>-7-(4-methoxybenzyloxy)-2,4,6-trimethyl-3,5-(2,4,6-trimethylbenzylidenedioxy)nonanal
• 英文别名: (2R,3S,4S,5R,6R,7R)-1-Benzoyloxy-6-[(1,1-dimethylethyl)dimethylsilyloxy]-7-(4-methoxybenzyloxy)-2,4,6-trimethyl-3,5-(2,4,6-trimethylbenzylidenedioxy)nonanal
• CAS: 131755-79-8
• 化学式: C₃₆H₅₆O₆Si
• 分子量: 612.923
• InChiKey: HBGFLVCUWGWDKY-IFZMCCAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.65
• 重原子数：
  43.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (2R,3S,4S,5R,6R,7R)-1-Benzoyloxy-6-<(1,1-dimethylethyl)dimethylsilyloxy>-7-(4-methoxybenzyloxy)-2,4,6-trimethyl-3,5-(2,4,6-trimethylbenzylidenedioxy)nonanal 在 Raney Ni (W-2) 正丁基锂 、 草酰氯 、 氢气 、 二甲基亚砜 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 35.17h， 生成 (3R,4S,5S,6R,7R,8R)-7-<(1,1-Dimethylethyl)dimethylsilyloxy>-8-(4-methoxybenzyloxy)-3,5,7-trimethyl-4,6-(2,4,6-trimethylbenzylidenedioxy)decanal
  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：

  (2R,3S,4S,5R,6R,7R)-1-Benzoyloxy-6-<(1,1-dimethylethyl)dimethylsilyloxy>-7-(4-methoxybenzyloxy)-2,4,6-trimethyl-3,5-(2,4,6-trimethylbenzylidenedioxy)nonane-1-ol 在 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以88%的产率得到(2R,3S,4S,5R,6R,7R)-1-Benzoyloxy-6-<(1,1-dimethylethyl)dimethylsilyloxy>-7-(4-methoxybenzyloxy)-2,4,6-trimethyl-3,5-(2,4,6-trimethylbenzylidenedioxy)nonanal
  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