tert.-butyl (6R,7R)-7-benzoylamino-3-methoxy-8-oxo-5-oxa-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate | 95967-31-0

• 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: tert.-butyl (6R,7R)-7-benzoylamino-3-methoxy-8-oxo-5-oxa-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate
• 英文别名: tert-butyl (6R,7R)-7-benzoylamino-3-methoxy-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate；tert.-Butyl (6R, 7R)-7-benzoylamino-3-methoxy-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate；tert-butyl (6R,7R)-7-benzamido-3-methoxy-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS: 95967-31-0
• 化学式: C₁₉H₂₂N₂O₆
• 分子量: 374.393
• InChiKey: PZDHDYZLCFMGQE-SUMWQHHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert.-butyl (6R,7R)-7-benzoylamino-3-methoxy-8-oxo-5-oxa-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate 生成 tert-butyl (6R,7R)-7-amino-3-methoxy-8-oxo-5-oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
  参考文献：
  名称：

  HAEBICH, D.;HARTWIG, W.

  摘要：

  DOI：
• 作为产物：
  描述：

  tert.-butyl (6R,7R)-7-benzoylamino-3-hydroxy-8-oxo-5-oxa-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate 生成 tert.-butyl (6R,7R)-7-benzoylamino-3-methoxy-8-oxo-5-oxa-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylate
  参考文献：
  名称：

  HAEBICH, D.;HARTWIG, W.

  摘要：

  DOI：

文献信息

• Process for the preparation of 7-acylamino-3-hydroxy-cephem-4-carboxylic
  申请人：Bayer Aktiengesellschaft

  公开号：US04616084A1

  公开（公告）日：1986-10-07

  A process for the preparation of a 7-acylamino-3-hydroxy-2-cephem-4-carboxylic acid, 7-acylamino-3-hydroxy-1-dethia-1-oxa-3-cephem-4-carboxylic acid or derivative thereof of the general formula ##STR1## in which R.sup.1 is hydrogen or optionally substituted alkyl, alkenyl, alkinyl, aralkyl, aryl, heteroaryl, heteroaralkyl, aryloxyalkyl, heteroaryloxyalkyl, alkoxyalkyl, arylthioalkyl, heteroarylthioalkyl, alkylthioalkyl, alkoxy, aryloxy, alkylthio or arylthio, R.sup.2 is hydrogen, a carboxy-protective group or a pharmaceutically useful ester radical, and X is sulphur or oxygen, which comprises: (a) reacting a compound of the formula ##STR2## with (i) a compound of the formula ##STR3## in which R.sup.2 and X have the abovementioned meaning and Y represents diazo (N.sub.2) or hydrogen (H.sub.2) in an inert solvent in the presence of a Lewis acid or proton acid catalyst, or (ii) a compound of the formula HX--CH.sub.2 --C.tbd.C--COOR.sup.2 to form an intemediate compound having a triple bond, and hydrating the triple bond, the compounds thus obtained, for Y being hydrogen (H.sub.2)--(in case of Y=diazo (N.sub.2) directly the compounds of general formula (2) are obtained) thereby to produce a compound of the formula ##STR4## (b) reacting such compound with an azide in a solvent in the presence of a base to give a compound of the formula ##STR5## (c) converting said compound to the desired product by (i) irradiation in an inert solvent, or (ii) warming in the presence of a catalyst. The end products are, or can be converted to, known .beta.-lactam antibiotics.

  一种制备7-酰氨基-3-羟基-2-头孢烯-4-羧酸，7-酰氨基-3-羟基-1-去硫-1-氧-3-头孢烯-4-羧酸或其衍生物的方法，其一般式为##STR1##其中R.sup.1为氢或可选择地取代的烷基，烯基，炔基，芳基烷基，芳基，杂环芳基，杂环芳基烷基，芳氧基烷基，杂环芳氧基烷基，烷氧基烷基，芳硫基烷基，杂环芳硫基烷基，烷硫基烷基，烷氧基，芳氧基，烷硫基或芳硫基，R.sup.2为氢，羧基保护基或药用酯基，X为硫或氧，包括以下步骤：(a)将式##STR2##的化合物与(i)式##STR3##的化合物在惰性溶剂中与路易斯酸或质子酸催化剂一起反应，其中R.sup.2和X具有上述含义，Y代表重氮（N.sub.2）或氢（H.sub.2），或(ii)式HX--CH.sub.2 --C.tbd.C--COOR.sup.2的化合物反应，形成具有三键的中间化合物，并水合三键，从而获得化合物，对于Y为氢（H.sub.2）时，（在Y=重氮（N.sub.2）的情况下直接获得一般式（2）的化合物），从而产生一种化合物##STR4##(b)在溶剂中在碱的存在下将此类化合物与叠氮反应，得到一种化合物##STR5##(c)通过（i）在惰性溶剂中照射，或（ii）在催化剂存在下加热将所述化合物转化为所需的产物。最终产物是已知的β-内酰胺类抗生素或可转化为其的化合物。
• A convergent scheme for the stereoselective synthesis of 3'-nor-1-oxacephems
  作者：D. Ha¨bich、W. Hartwig

  DOI：10.1016/s0040-4020(01)88797-4

  日期：1984.1
• HAEBICH, D.;HARTWIG, W.
  作者：HAEBICH, D.、HARTWIG, W.

  DOI：——

  日期：——