[(S)-1-((3aR,4S,6R,6aS)-6-Hydroxy-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester | 160057-26-1

• 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,6aS)-6-Hydroxy-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[(2S)-1-[[(3aS,4R,6S,6aR)-4-hydroxy-2,2-dimethyl-4,5,6,6a-tetrahydro-3aH-cyclopenta[d][1,3]dioxol-6-yl]amino]-1-oxopropan-2-yl]carbamate
• CAS: 160057-26-1
• 化学式: C₁₆H₂₈N₂O₆
• 分子量: 344.408
• InChiKey: DROZSTWMSLESTN-HGCLJGPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  106
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 [(S)-1-((3aR,4S,6R,6aS)-6-Hydroxy-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-ylcarbamoyl)-ethyl]-carbamic acid tert-butyl ester 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以83%的产率得到1(R)-Acetoxy-2(R),3(R)-(isopropylidenedioxy)-4(S)-amino>cyclopentane
  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：

  [(R)-2-((1S,4R,6R)-5,6-Dihydroxy-2-oxa-3-aza-bicyclo[2.2.1]hept-3-yl)-1-methyl-2-oxo-ethyl]-carbamic acid tert-butyl ester 在 hexacarbonyl molybdenum 、 对甲苯磺酸 作用下， 以 水 、 乙腈 为溶剂， 反应 1.0h， 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