(2R,4aR,5aR,9aS)-6-hydroxy-6-(1-hydroxy-1-methylethyl)-2-phenyl-1,3,5-trioxa-8-azacyclobuta[b]decalin-7-one | 916676-80-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: (2R,4aR,5aR,9aS)-6-hydroxy-6-(1-hydroxy-1-methylethyl)-2-phenyl-1,3,5-trioxa-8-azacyclobuta[b]decalin-7-one
• CAS: 916676-80-7
• 化学式: C₁₇H₂₁NO₆
• 分子量: 335.357
• InChiKey: MFJCWRKGFRUEKW-ADZTWHKLSA-N

反应信息

• 作为反应物：
  描述：

  (2R,4aR,5aR,9aS)-6-hydroxy-6-(1-hydroxy-1-methylethyl)-2-phenyl-1,3,5-trioxa-8-azacyclobuta[b]decalin-7-one 在 palladium on activated charcoal 吡啶 、 sodium tetrahydroborate 、 氢气 、 高碘酸 作用下， 以 甲醇 、 水 、 乙酸乙酯 为溶剂， 反应 3.25h， 生成 (3S,4R,6R,7S)-3-benzoyloxy-4-(benzoyloxymethyl)-7-hydroxy-5-oxacepham
  参考文献：
  名称：

  An entry to 7-amino- and to 2-ethoxycarbonyl-5-dethia-5-oxa-cephams from 1,3-alkylidene-l-erythritol

  摘要：

  The alkoxyallene derived from 1,3-benzylidene-L-erythritol when treated with chlorosulfonyl isocyanate provided diastereomeric beta-lactams with moderate stereoselectivity. After the intramolecular alkylation of the nitrogen atom, these afforded compounds having oxacepham skeletons. The exo-isopropylidene group enabled the introduction of a variety of substituents to the C-7 carbon atom of the cepham, whereas removal of the benzylidene protection followed by the oxidation of 3-OH to the ketone allowed carboxylation of the C-2 carbon atom. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.08.074
• 作为产物：
  描述：

  (2R,4aR,5aR,8aS)-6-isopropylidene-2-phenyl-1,3,5-trioxa-7a-azacyclobuta[b]decalin-7-one 在 ruthenium trichloride 、 sodium periodate 作用下， 以 氯仿 、 水 、 乙腈 为溶剂， 反应 0.5h， 以87%的产率得到(2R,4aR,5aR,9aS)-6-hydroxy-6-(1-hydroxy-1-methylethyl)-2-phenyl-1,3,5-trioxa-8-azacyclobuta[b]decalin-7-one
  参考文献：
  名称：

  An entry to 7-amino- and to 2-ethoxycarbonyl-5-dethia-5-oxa-cephams from 1,3-alkylidene-l-erythritol

  摘要：

  The alkoxyallene derived from 1,3-benzylidene-L-erythritol when treated with chlorosulfonyl isocyanate provided diastereomeric beta-lactams with moderate stereoselectivity. After the intramolecular alkylation of the nitrogen atom, these afforded compounds having oxacepham skeletons. The exo-isopropylidene group enabled the introduction of a variety of substituents to the C-7 carbon atom of the cepham, whereas removal of the benzylidene protection followed by the oxidation of 3-OH to the ketone allowed carboxylation of the C-2 carbon atom. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.08.074