(E)-(4R,5R)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hex-2-enoic acid methyl ester | 216868-19-8

• 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: (E)-(4R,5R)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hex-2-enoic acid methyl ester
• 英文别名: methyl (E,4R,5R)-5-[tert-butyl(dimethyl)silyl]oxy-4-methyl-6-phenylmethoxyhex-2-enoate
• CAS: 216868-19-8
• 化学式: C₂₁H₃₄O₄Si
• 分子量: 378.584
• InChiKey: KOYHSHCAAOXZQW-WXVNRZFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.96
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-(4R,5R)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hex-2-enoic acid methyl ester 在 四氧化锇 、 N-甲基吲哚酮 作用下， 以 水 、 丙酮 、 叔丁醇 为溶剂， 反应 4.0h， 生成 (2R,3S,4R,5R)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2,3-dihydroxy-4-methyl-hexanoic acid methyl ester 、 (2S,3R,4R,5R)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-2,3-dihydroxy-4-methyl-hexanoic 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：

  (R)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-butyric acid isopropyl ester 在 二异丁基氢化铝 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 二氯甲烷 、 环己烷 为溶剂， 反应 22.5h， 生成 (E)-(4R,5R)-6-Benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-4-methyl-hex-2-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