(2E,4E)-(6R,7R)-7-(tert-Butyl-dimethyl-silanyloxy)-7-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-methyl-hepta-2,4-dienoic acid methyl ester | 216868-31-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (2E,4E)-(6R,7R)-7-(tert-Butyl-dimethyl-silanyloxy)-7-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-methyl-hepta-2,4-dienoic acid methyl ester
• 英文别名: methyl (2E,4E,6R,7R)-7-[tert-butyl(dimethyl)silyl]oxy-7-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-methylhepta-2,4-dienoate
• CAS: 216868-31-4
• 化学式: C₂₀H₃₆O₅Si
• 分子量: 384.588
• InChiKey: DUPGYMRERGKREN-QFKVHAOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.45
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2E,4E)-(6R,7R)-7-(tert-Butyl-dimethyl-silanyloxy)-7-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-methyl-hepta-2,4-dienoic acid methyl ester 在 四氧化锇 、 甲基磺酰胺 、 potassium carbonate 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 potassium hexacyanoferrate(III) 作用下， 以 水 、 叔丁醇 为溶剂， 反应 21.0h， 以41%的产率得到(E)-(2S,3R,6R,7R)-7-(tert-Butyl-dimethyl-silanyloxy)-7-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,3-dihydroxy-6-methyl-hept-4-enoic acid methyl ester
  参考文献：
  名称：

  An efficient protocol for the stereoselective dihydroxylation of ene-ester systems

  摘要：

  Dihydroxylation of ene ester systems was achieved in good yield and diastereoselectivity under classical catalytic OsO4 and NMO conditions using the intrinsic diastereoselectivity in alpha-methyl beta-OTBS systems. This intrinsic diastereoselection can be reversed using 'super' AD-mix to give the opposite diastereomer also in good selectivity. The regioselection of dihydroxylation in diene esters using a modified 'super' AD-mix was poor. This methodology can be applied towards the synthesis of part structures of the marine macrolide Altohyrtin A. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00800-x
• 作为产物：
  描述：

  (E)-(4R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-4-methyl-pent-2-enoic acid methyl ester 在 二异丁基氢化铝 、 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 18.5h， 生成 (2E,4E)-(6R,7R)-7-(tert-Butyl-dimethyl-silanyloxy)-7-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-6-methyl-hepta-2,4-dienoic acid methyl ester
  参考文献：
  名称：

  An efficient protocol for the stereoselective dihydroxylation of ene-ester systems

  摘要：

  Dihydroxylation of ene ester systems was achieved in good yield and diastereoselectivity under classical catalytic OsO4 and NMO conditions using the intrinsic diastereoselectivity in alpha-methyl beta-OTBS systems. This intrinsic diastereoselection can be reversed using 'super' AD-mix to give the opposite diastereomer also in good selectivity. The regioselection of dihydroxylation in diene esters using a modified 'super' AD-mix was poor. This methodology can be applied towards the synthesis of part structures of the marine macrolide Altohyrtin A. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00800-x