(4R)-4-benzyl-3-[(E,2R,3S)-5-[(2R,4R,5R)-2-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]-5-prop-2-enyl-4-(2-trityloxyethyl)-1,3-dioxolan-4-yl]-2-ethyl-3-triethylsilyloxypent-4-enoyl]-1,3-oxazolidin-2-one | 1053731-78-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (4R)-4-benzyl-3-[(E,2R,3S)-5-[(2R,4R,5R)-2-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]-5-prop-2-enyl-4-(2-trityloxyethyl)-1,3-dioxolan-4-yl]-2-ethyl-3-triethylsilyloxypent-4-enoyl]-1,3-oxazolidin-2-one
• CAS: 1053731-78-4
• 化学式: C₆₂H₇₉NO₈Si₂
• 分子量: 1022.48
• InChiKey: QHJSFQRSNKXUHT-SLVFWNKASA-N

物化性质

• 沸点：
  916.3±65.0 °C(Predicted)
• 密度：
  1.096±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  14.76
• 重原子数：
  73
• 可旋转键数：
  25
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  92.8
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (4R)-4-benzyl-3-[(E,2R,3S)-5-[(2R,4R,5R)-2-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]-5-prop-2-enyl-4-(2-trityloxyethyl)-1,3-dioxolan-4-yl]-2-ethyl-3-triethylsilyloxypent-4-enoyl]-1,3-oxazolidin-2-one 在 四丁基氢氧化铵 、 4-甲基苯磺酸吡啶 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 甲苯 为溶剂， 反应 6.0h， 生成 ethyl (2Z,4S,5S,6E)-7-{(2R,4R,5R)-5-allyl-2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-4-[2-(tritylioxy)ethyl]-[1,3]dioxolan-4-yl}-4-ethyl-5-hydroxyhepta-2,6-dienoate
  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 吡啶 、 咪唑 、 甲醇 、 4-二甲氨基吡啶 、 manganese(IV) oxide 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 4 A molecular sieve 、 三氟甲磺酸二丁硼 、 camphor-10-sulfonic acid 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 二异丁基氢化铝 、 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 38.43h， 生成 (4R)-4-benzyl-3-[(E,2R,3S)-5-[(2R,4R,5R)-2-[4-[tert-butyl(dimethyl)silyl]oxyphenyl]-5-prop-2-enyl-4-(2-trityloxyethyl)-1,3-dioxolan-4-yl]-2-ethyl-3-triethylsilyloxypent-4-enoyl]-1,3-oxazolidin-2-one
  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).