{(S)-1-[(3aR,4S,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxy)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester | 160057-25-0

• 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: {(S)-1-[(3aR,4S,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxy)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester
• CAS: 160057-25-0
• 化学式: C₃₂H₄₆N₂O₆Si
• 分子量: 582.813
• InChiKey: RFFNKXAJHKOTQV-ZYMCBDGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.25
• 重原子数：
  41.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  95.12
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  {(S)-1-[(3aR,4S,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxy)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ylcarbamoyl]-ethyl}-carbamic acid tert-butyl ester 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以81%的产率得到[(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：

  BOC-L-丙氨酸甲酯 在 咪唑 、 氢氧化钾 、 四氧化锇 、 hexacarbonyl molybdenum 、 盐酸羟胺 、 四丁基高碘酸铵 、 对甲苯磺酸 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 乙腈 、 叔丁醇 为溶剂， 反应 35.5h， 生成 {(S)-1-[(3aR,4S,6R,6aR)-6-(tert-Butyl-diphenyl-silanyloxy)-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