(2R,3S,5R,6R) 2-(N-Acetyl)carbamoyloxymethyl-6-amino2-methylpenam-3-carboxylic Acid p-Nitrobenzyl Ester | 74555-03-6

• 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: (2R,3S,5R,6R) 2-(N-Acetyl)carbamoyloxymethyl-6-amino2-methylpenam-3-carboxylic Acid p-Nitrobenzyl Ester
• 英文别名: (4-nitrophenyl)methyl (2S,3R,5R,6R)-3-(acetylcarbamoyloxymethyl)-6-amino-3-methyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
• CAS: 74555-03-6
• 化学式: C₁₈H₂₀N₄O₈S
• 分子量: 452.445
• InChiKey: SVKHLWRBLIGSRS-OSDKZWGASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  199
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2R,3S,5R,6R) 2-(N-Acetyl)carbamoyloxymethyl-6-amino2-methylpenam-3-carboxylic Acid p-Nitrobenzyl Ester 、 氢气 在 钯 乙酸乙酯 、 水 、 白碳黑 作用下， 以 水 为溶剂， 反应 1.33h， 以There was obtained 0.38 gm of the title compound as a white amorphous solid的产率得到(2R,3S,5R,6R) 2-(N-Acetyl)carbamoyloxymethyl-6-amino-2-methylpenam-3-carboxylic Acid
  参考文献：
  名称：

  Process for producing carbamoyl substituted penams and carbamoyl

  摘要：

  青霉素亚砜酯与异氰酸酯反应，生成相应的（取代）-2-氨氧甲基青霉烯，相应的（取代）-3-氨氧甲基头孢菌素或相应的3-甲基头孢菌素。这些产物的6-或7-侧链可以裂解，以给出相应的6-氨基（青霉烯）或7-氨基（头孢菌素和头孢菌素）化合物，后者可以重新酰化以产生不同的6-酰基-2-氨氧甲基青霉烯，7-酰基-3-氨氧甲基头孢菌素和7-酰基-3-甲基头孢菌素。 取代基团可以从（取代）-2-氨氧甲基青霉烯或（取代）-3-氨氧甲基头孢菌素中去除，以分别得到相应的自由2-氨氧甲基青霉烯或3-氨氧甲基头孢菌素。

  公开号：

  US04310459A1
• 作为产物：
  描述：

  (2R,3S,5R,6R) 2-(N-acetyl)carbamoyloxymethyl-2-methyl-6-phenoxyacetamidopenam-3-carboxylic acid p-nitrobenzyl ester 在 五氯化磷 、 2,3-二甲基苯胺 作用下， 以 甲醇 、 ice-water 、 正庚烷 、 二氯甲烷 为溶剂， 生成 (2R,3S,5R,6R) 2-(N-Acetyl)carbamoyloxymethyl-6-amino2-methylpenam-3-carboxylic Acid p-Nitrobenzyl Ester
  参考文献：
  名称：

  Process for producing carbamoyl substituted penams and carbamoyl

  摘要：

  盼西林亚砜酯与异氰酸酯反应，生成相应的（取代）-2-氨基羧甲基青霉素，相应的（取代）-3-氨基羧甲氧头孢菌素或相应的3-甲基头孢菌素。这些产物的6-或7-侧链可以被裂解，得到相应的6-氨基（青霉素）或7-氨基（头孢菌素和头孢菌素）化合物，后者可以重新酰化，产生不同的6-酰基-2-氨基羧甲基青霉素，7-酰基-3-氨基羧甲氧头孢菌素和7-酰基-3-甲基头孢菌素。这些取代基团可以从（取代）-2-氨基羧甲氧青霉素或（取代）-3-氨基羧甲氧头孢菌素中去除，分别得到相应的游离2-氨基羧甲基青霉素或3-氨基羧甲氧头孢菌素。

  公开号：

  US04310459A1

文献信息

• 6-Amino penam derivatives
  申请人：Bristol-Myers Company

  公开号：US04407755A1

  公开（公告）日：1983-10-04

  Penicillin sulfoxide esters are reacted with an isocyanate to produce the corresponding (substituted)-2-carbamoyloxymethylpenam, the corresponding (substituted)-3-carbamoyloxycepham or the corresponding 3-methylcephem. The 6- or 7-side-chain of these products may be cleaved to give the corresponding 6-amino (penams) or 7-amino (cephams and cephems) compounds, and the latter may be reacylated to produce different 6-acyl-2-carbamoyloxymethyl penams, 7-acyl-3-carbamoyloxy cephams and 7-acyl-3-methylcephems. The substituent groups may be removed from the (substituted)-2-carbamoyloxypenams or the (substituted)-3-carbamoyloxycephams to give the corresponding free 2-carbamoyloxymethylpenams or 3-carbamoyloxycephams, respectively.

  青霉素亚砜酯与异氰酸酯反应，可产生相应的（取代）-2-氨氧甲基青霉烯，相应的（取代）-3-氨氧甲基头孢菌素或相应的3-甲基头孢菌素。这些产物的6-或7-侧链可以裂解，从而得到相应的6-氨基（青霉烯）或7-氨基（头孢菌素和头孢菌素）化合物，后者可以重新酰化以产生不同的6-酰基-2-氨氧甲基青霉烯，7-酰基-3-氨氧甲基头孢菌素和7-酰基-3-甲基头孢菌素。取代基团可以从（取代）-2-氨氧甲基青霉烯或（取代）-3-氨氧甲基头孢菌素中去除，以得到相应的自由2-氨氧甲基青霉烯或3-氨氧甲基头孢菌素。
• 3-Carbamoyloxy-cepham-4-carboxylic acid derivatives
  申请人：Bristol-Myers Company

  公开号：US04426520A1

  公开（公告）日：1984-01-17

  Penicillin sulfoxide esters are reacted with an isocyanate to produce the corresponding (substituted)-2-carbamoyloxymethylpenam, the corresponding (substituted)-3-carbamoyloxycepham or the corresponding 3-methylcepem. The 6- or 7-side-chain of these products may be cleaved to give the corresponding 6-amino (penams) or 7-amino (cephams and cephems) compounds, and the latter may be reacylated to produce different 6-acyl-2-carbamoyloxymethyl penams, 7-acyl-3-carbamoyloxy cephams and 7-acyl-3-methylcephems. The substituent groups may be removed from the (substituted)-2-carbamoyloxypenams or the (substituted)-3-carbamoyloxycephams to give the corresponding free 2-carbamoyloxymethylpenams or 3-carbamoyloxycephams, respectively.

  青霉素磺酰氧酯与异氰酸酯反应，得到相应的（取代）-2-氨氧甲基青霉烯、相应的（取代）-3-氨氧甲基头孢菌素或相应的3-甲基头孢烯。这些产物的6-或7-侧链可被裂解，以得到相应的6-氨基（青霉烯）或7-氨基（头孢菌素和头孢烯）化合物，后者可被重新酰化以产生不同的6-酰基-2-氨氧甲基青霉烯、7-酰基-3-氨氧甲基头孢菌素和7-酰基-3-甲基头孢烯。取代基团可以从（取代）-2-氨氧甲基青霉烯或（取代）-3-氨氧甲基头孢菌素中去除，以分别得到相应的自由2-氨氧甲基青霉烯或3-氨氧甲基头孢菌素。
• 2-Carbamoyloxymethyl-penicillin derivatives
  申请人：Bristol-Myers Company

  公开号：US04322347A1

  公开（公告）日：1982-03-30

  Penicillin sulfoxide esters are reacted with an isocyanate to produce the corresponding (substituted)-2-carbamoyloxymethylpenam, the corresponding (substituted)-3-carbamoyloxycepham or the corresponding 3-methylcephem. The 6- or 7-side-chain of these products may be cleaved to give the corresponding 6-amino (penams) or 7-amino (cephams and cephems) compounds, and the latter may be reacylated to produce different 6-acyl-2-carbamoyloxymethyl penams, 7-acyl-3-carbamoyloxy cephams and 7-acyl-3-methylcephems. The substituent groups may be removed from the (substituted)-2-carbamoyloxypenams or the (substituted)-3-carbamoyloxycephams to give the corresponding free 2-carbamoyloxymethylpenams or 3-carbamoyloxycephams, respectively.

  青霉素硫氧化物酯与异氰酸酯反应，可以产生相应的（取代）-2-氨氧甲基青霉烯，相应的（取代）-3-氨氧甲基头孢菌素或相应的3-甲基头孢菌素。这些产物的6-或7-侧链可以被裂解，以得到相应的6-氨基（青霉烯）或7-氨基（头孢菌素和头孢菌素）化合物，后者可以重新酰化以产生不同的6-酰基-2-氨氧甲基青霉烯，7-酰基-3-氨氧甲基头孢菌素和7-酰基-3-甲基头孢菌素。取代基可以从（取代）-2-氨氧甲基青霉烯或（取代）-3-氨氧甲基头孢菌素中去除，以分别得到相应的自由2-氨氧甲基青霉烯或3-氨氧甲基头孢菌素。
• Cepham compounds
  申请人：Bristol-Myers Company

  公开号：US04374982A1

  公开（公告）日：1983-02-22

  Penicillin sulfoxide esters are reacted with an isocyanate to produce the corresponding (substituted)-2-carbamoyloxymethylpenam, the corresponding (substituted)-3-carbamoyloxycepham or the corresponding 3-methylcephem. The 6- or 7-side-chain of these products may be cleaved to give the corresponding 6-amino (penams) or 7-amino (cephams and cephems) compounds, and the latter may be reacylated to produce different 6-acyl-2-carbamoyloxymethyl penams, 7-acyl-3-carbamoyloxy cephams and 7-acyl-3-methylcephems. The substituent groups may be removed from the (substituted)-2-carbamoyloxypenams or the (substituted)-3-carbamoyloxycephams to give the corresponding free 2-carbamoyloxymethylpenams or 3-carbamoyloxycephams, respectively.

  青霉素亚砜酯与异氰酸酯反应，得到相应的（取代基）-2-氨氧甲基青霉烯，相应的（取代基）-3-氨氧甲基头孢菌素或相应的3-甲基头孢菌素。这些产物的6-或7-侧链可以裂解，得到相应的6-氨基（青霉烯）或7-氨基（头孢菌素和头孢菌素）化合物，后者可以重新酰化，产生不同的6-酰基-2-氨氧甲基青霉烯，7-酰基-3-氨氧甲基头孢菌素和7-酰基-3-甲基头孢菌素。取代基可以从（取代基）-2-氨氧甲基青霉烯或（取代基）-3-氨氧甲基头孢菌素中去除，得到相应的自由2-氨氧甲基青霉烯或3-氨氧甲基头孢菌素。
• US4310459A
  申请人：——

  公开号：US4310459A

  公开（公告）日：1982-01-12