(3S,4R,6R,7S)-3-hydroxy-4-(hydroxymethyl)-7-methyl-5-oxacepham | 478288-87-8

• 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: (3S,4R,6R,7S)-3-hydroxy-4-(hydroxymethyl)-7-methyl-5-oxacepham
• 英文别名: (3S,4R,6R,7S)-3-hydroxy-4-(hydroxymethyl)-7-methyl-5-oxa-1-azabicyclo[4.2.0]octan-8-one
• CAS: 478288-87-8
• 化学式: C₈H₁₃NO₄
• 分子量: 187.196
• InChiKey: UUEQQQLOTKRUNR-BYPJNBLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  70
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (3S,4R,6R,7S)-3-hydroxy-4-(hydroxymethyl)-7-methyl-5-oxacepham 在 吡啶 作用下， 生成 Acetic acid (3S,4R,6R,7S)-4-acetoxymethyl-7-methyl-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]oct-3-yl ester
  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：

  1,3-O-benzylidene-2-O-[(3S,4R)-3-methyl-2-oxoazetidin-4-yl]-4-O-(trityloxymethyl)-L-erythritol 在 palladium on activated charcoal 吡啶 、 四丁基溴化铵 、 氢气 、 potassium carbonate 、 对甲苯磺酸 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 1.5h， 生成 (3S,4R,6R,7S)-3-hydroxy-4-(hydroxymethyl)-7-methyl-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

文献信息

• An entry to 7-amino- and to 2-ethoxycarbonyl-5-dethia-5-oxa-cephams from 1,3-alkylidene-l-erythritol
  作者：Tong Thanh Danh、Katarzyna Borsuk、Jolanta Solecka、Marek Chmielewski

  DOI：10.1016/j.tet.2006.08.074

  日期：2006.11

  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.