1(R)-1-<(tert-Butyldiphenylsilyl)oxy>-4(S)-cyclopent-2-ene | 160057-21-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1(R)-1-<(tert-Butyldiphenylsilyl)oxy>-4(S)-cyclopent-2-ene
• 英文别名: tert-butyl N-[(2S)-1-[[(1S,4R)-4-[tert-butyl(diphenyl)silyl]oxycyclopent-2-en-1-yl]amino]-1-oxopropan-2-yl]carbamate
• CAS: 160057-21-6
• 化学式: C₂₉H₄₀N₂O₄Si
• 分子量: 508.733
• InChiKey: OMKHPBGHCFTKMN-ZRBLBEILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.29
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  76.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1(R)-1-<(tert-Butyldiphenylsilyl)oxy>-4(S)-cyclopent-2-ene 在 四氧化锇 、 四丁基氟化铵 、 对甲苯磺酸 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 叔丁醇 为溶剂， 反应 15.25h， 生成 [(S)-1-((3aR,4S,6R,6aS)-6-Hydroxy-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Amino Acid-Derived Chiral Acyl Nitroso Compounds: Diastereoselectivity in Intermolecular Hetero Diels-Alder Reactions

  摘要：

  The diastereoselectivities of chiral acyl nitroso dienophiles derived from optically pure N-protected alpha-amino hydroxamic acids have been determined in intermolecular hetero Diels-Alder reactions. The cycloaddition reactions afforded synthetically useful quantities of functionally rich, optically pure cycloadducts, useful for the preparation of a variety of compounds of potential biological interest. Molybdenum hexacarbonyl reduction of the cycloadducts gave optically pure allylic alcohols. Osmium tetraoxide-catalyzed dihydroxylation of several bis-allylically substituted intermediates gave only the diastereomerically pure diols corresponding to naturally occurring 2',3'-dihydroxynucleoside analogs.

  DOI：

  10.1021/jo00095a040
• 作为产物：
  描述：

  (S)-tert-butyl 1-(hydroxyamino)-1-oxopropan-2-ylcarbamate 在 咪唑 、 hexacarbonyl molybdenum 、 四丁基高碘酸铵 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 21.0h， 生成 1(R)-1-<(tert-Butyldiphenylsilyl)oxy>-4(S)-cyclopent-2-ene
  参考文献：
  名称：

  Amino Acid-Derived Chiral Acyl Nitroso Compounds: Diastereoselectivity in Intermolecular Hetero Diels-Alder Reactions

  摘要：

  The diastereoselectivities of chiral acyl nitroso dienophiles derived from optically pure N-protected alpha-amino hydroxamic acids have been determined in intermolecular hetero Diels-Alder reactions. The cycloaddition reactions afforded synthetically useful quantities of functionally rich, optically pure cycloadducts, useful for the preparation of a variety of compounds of potential biological interest. Molybdenum hexacarbonyl reduction of the cycloadducts gave optically pure allylic alcohols. Osmium tetraoxide-catalyzed dihydroxylation of several bis-allylically substituted intermediates gave only the diastereomerically pure diols corresponding to naturally occurring 2',3'-dihydroxynucleoside analogs.

  DOI：

  10.1021/jo00095a040

文献信息

• Amino Acid-Derived Chiral Acyl Nitroso Compounds: Diastereoselectivity in Intermolecular Hetero Diels-Alder Reactions
  作者：Allen R. Ritter、Marvin J. Miller

  DOI：10.1021/jo00095a040

  日期：1994.8

  The diastereoselectivities of chiral acyl nitroso dienophiles derived from optically pure N-protected alpha-amino hydroxamic acids have been determined in intermolecular hetero Diels-Alder reactions. The cycloaddition reactions afforded synthetically useful quantities of functionally rich, optically pure cycloadducts, useful for the preparation of a variety of compounds of potential biological interest. Molybdenum hexacarbonyl reduction of the cycloadducts gave optically pure allylic alcohols. Osmium tetraoxide-catalyzed dihydroxylation of several bis-allylically substituted intermediates gave only the diastereomerically pure diols corresponding to naturally occurring 2',3'-dihydroxynucleoside analogs.