(3S,4R,6S)-3-benzoyloxy-4-(benzoyloxymethyl)-7-hydroxy-7-(1-hydroxy-1-methylethyl)-5-oxacepham | 916676-84-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,4R,6S)-3-benzoyloxy-4-(benzoyloxymethyl)-7-hydroxy-7-(1-hydroxy-1-methylethyl)-5-oxacepham
• 英文别名: [(3S,4R,6S)-3-benzoyloxy-7-hydroxy-7-(2-hydroxypropan-2-yl)-8-oxo-5-oxa-1-azabicyclo[4.2.0]octan-4-yl]methyl benzoate
• CAS: 916676-84-1
• 化学式: C₂₄H₂₅NO₈
• 分子量: 455.464
• InChiKey: YUIYGOBJEKKNCG-ARMJMNSUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  33
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  123
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3S,4R,6S)-3-benzoyloxy-4-(benzoyloxymethyl)-7-hydroxy-7-(1-hydroxy-1-methylethyl)-5-oxacepham 在 高碘酸 作用下， 以 乙酸乙酯 为溶剂， 反应 0.75h， 生成
  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,5aS,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 、 氢气 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 (3S,4R,6S)-3-benzoyloxy-4-(benzoyloxymethyl)-7-hydroxy-7-(1-hydroxy-1-methylethyl)-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