(2S,3R,4S)-3-(3,4-Dimethoxybenzyloxy)-1-<(1,1-dimethylethyl)diphenylsilyloxy>-2,4-dimethyl-5-methylsulfonyloxypentane | 131755-73-2

• 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)-3-(3,4-Dimethoxybenzyloxy)-1-<(1,1-dimethylethyl)diphenylsilyloxy>-2,4-dimethyl-5-methylsulfonyloxypentane
• CAS: 131755-73-2
• 化学式: C₃₃H₄₆O₇SSi
• 分子量: 614.876
• InChiKey: YSZMUYJBHMDALQ-ZDQHWEPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.41
• 重原子数：
  42.0
• 可旋转键数：
  15.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  80.29
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,4S)-3-(3,4-Dimethoxybenzyloxy)-1-<(1,1-dimethylethyl)diphenylsilyloxy>-2,4-dimethyl-5-methylsulfonyloxypentane 在 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 (2S,3R,4S)-3-(3,4-Dimethoxybenzyloxy)-1-<(1,1-dimethylethyl)diphenylsilyloxy>-2,4-dimethyl-5-phenylsulfonylpentane
  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：

  (2S,3R,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-3-(3,4-dimethoxy-benzyloxy)-2,4-dimethyl-pentan-1-ol 、 甲基磺酰氯 以 二氯甲烷 为溶剂， 反应 14.0h， 以96%的产率得到(2S,3R,4S)-3-(3,4-Dimethoxybenzyloxy)-1-<(1,1-dimethylethyl)diphenylsilyloxy>-2,4-dimethyl-5-methylsulfonyloxypentane
  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