ethyl (2E)-3-[(4R)-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,2-dimethyl-[1,3]dioxan-4-yl]acrylate | 521274-38-4

• 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: ethyl (2E)-3-[(4R)-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,2-dimethyl-[1,3]dioxan-4-yl]acrylate
• 英文别名: ethyl (E)-3-[(4R)-4-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxan-4-yl]prop-2-enoate
• CAS: 521274-38-4
• 化学式: C₁₈H₃₄O₅Si
• 分子量: 358.55
• InChiKey: PCHJGGGLJOAIDJ-ZGKFYVQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 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：

  ethyl (2E)-3-[(4R)-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,2-dimethyl-[1,3]dioxan-4-yl]acrylate 在 碳酸氢钠 吡啶 、 咪唑 、 lead(IV) acetate 、 titanium(IV) isopropylate 、 三乙基硅烷 、 4-二甲氨基吡啶 、 manganese(IV) oxide 、 potassium osmate(VI) 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 三(2-氯乙基)胺 、 Br₂Cu^(1-)*Li⁽¹⁺⁾ 、 4 A molecular sieve 、 三氟甲磺酸二丁硼 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 四丁基氢氧化铵 、 水 、 4-甲基苯磺酸吡啶 、 二异丁基氢化铝 、 potassium carbonate 、 溶剂黄146 、 triethylamine tris(hydrogen fluoride) 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 N,N-二异丙基乙胺 、 三苯基膦 、 zinc dibromide 、 potassium hexacyanoferrate(III) 、 锌 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 、 叔丁醇 、 苯 为溶剂， 反应 166.93h， 生成 (1R,2Z,4Z)-1-{(2R,3R,4E)-3-(2-{[(allyloxyl)carbonyl]amino}ethyl)-5-[(2S,3S)-3-ethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl]-2,3-dihydroxypent-4-enyl}-5-{(1R,3S)-3-[(4-methoxyphenoxy)methyl]cyclohexyl}penta-2,4-dienyl phenoxyacetate
  参考文献：
  名称：

  Total Synthesis of Leustroducsin B

  摘要：

  A convergent total synthesis of leustroducsin B (1), which is known to exhibit a variety of biological activities, was successfully carried out. Notable features of our synthesis include construction of the C8 stereocenter by lipase-mediated desymmetrization of meso-diol 4 (90.2% ee) and preparation of the C9-C11 anti-diol moiety by the addition of alkynylzinc reagent 20 to the aldehyde 19. Furthermore, a new diol protecting group, p-silyloxybenzylidene, was developed for the deprotection from densely functionalized substrates under weakly acidic conditions. The protecting group was easily removed in a two-step procedure ((HF)3.Et3N; AcOH-THF-H2O).

  DOI：

  10.1021/ja0340679
• 作为产物：
  描述：

  [(4R)-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,2-dimethyl-[1,3]dioxan-4-yl]methyl acetate 在 甲醇 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 4 A molecular sieve 、 potassium carbonate 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 14.67h， 生成 ethyl (2E)-3-[(4R)-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)-2,2-dimethyl-[1,3]dioxan-4-yl]acrylate
  参考文献：
  名称：

  Total Synthesis of Leustroducsin B

  摘要：

  A convergent total synthesis of leustroducsin B (1), which is known to exhibit a variety of biological activities, was successfully carried out. Notable features of our synthesis include construction of the C8 stereocenter by lipase-mediated desymmetrization of meso-diol 4 (90.2% ee) and preparation of the C9-C11 anti-diol moiety by the addition of alkynylzinc reagent 20 to the aldehyde 19. Furthermore, a new diol protecting group, p-silyloxybenzylidene, was developed for the deprotection from densely functionalized substrates under weakly acidic conditions. The protecting group was easily removed in a two-step procedure ((HF)3.Et3N; AcOH-THF-H2O).

  DOI：

  10.1021/ja0340679

文献信息

• Total Synthesis of Leustroducsin B
  作者：Kousei Shimada、Yosuke Kaburagi、Tohru Fukuyama

  DOI：10.1021/ja0340679

  日期：2003.4.1

  A convergent total synthesis of leustroducsin B (1), which is known to exhibit a variety of biological activities, was successfully carried out. Notable features of our synthesis include construction of the C8 stereocenter by lipase-mediated desymmetrization of meso-diol 4 (90.2% ee) and preparation of the C9-C11 anti-diol moiety by the addition of alkynylzinc reagent 20 to the aldehyde 19. Furthermore, a new diol protecting group, p-silyloxybenzylidene, was developed for the deprotection from densely functionalized substrates under weakly acidic conditions. The protecting group was easily removed in a two-step procedure ((HF)3.Et3N; AcOH-THF-H2O).