68314-04-5

Upstream product

• 83273-83-0 diphenylmethyl 7α-benzoylamino-3β-phenylthio-3α-chloromethyl-1-oxacepham-4α-carboxylate 
• 83262-30-0 diphenylmethyl 7α-benzoylamino-3β-phenylseleno-3α-chloromethyl-1-oxacepham-4α-carboxylate 
• 1186615-53-1 (2S,6R,7R)-7-Benzoylamino-3-chloro-3-chloromethyl-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzhydryl ester 
• 77210-12-9 (2R,3R,6R,7R)-7-Benzoylamino-3-chloromethyl-3-hydroxy-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzhydryl ester 
• 77210-11-8 (2R,3S,6R,7R)-7-Benzoylamino-3-chloromethyl-3-hydroxy-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzhydryl ester 
• 67977-79-1 (R)-3-chloromethyl-2-((1R)-7-oxo-3-phenyl-(1rH,5cH)-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-but-3-enoic acid benzhydryl ester 
• 68313-69-9 Diphenylmethyl-2-(1R,5S-3-phenyl-7-oxo-4-oxa-2,6-diazabicyclo<3.2.0>hept-2-en-6-yl)-3,4-dihydroxy-3-chlormethylbutyrat 
• 67977-61-1 epi-Secopenicillin 
• 69780-18-3 6-epipenicillin sulfoxide 
• 67977-88-2 (R)-3-Hydroxymethyl-2-((1R,5S)-7-oxo-3-phenyl-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-but-3-enoic acid benzhydryl ester 
• 74242-86-7 Diphenylmethyl-2-(3R,4R-3-benzamido-4-chlor-2-oxo-azetidin-1-yl)-3-chlormethyl-3-butenoat 
• 67977-90-6 (R)-3-Nitrooxymethyl-2-((1R,5S)-7-oxo-3-phenyl-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-but-3-enoic acid benzhydryl ester 
• 67977-85-9 (R)-2-((1R,5S)-7-Oxo-3-phenyl-4-oxa-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-3-phenylsulfanylmethyl-but-3-enoic acid benzhydryl ester 
• 67977-91-7 (2R,6R,7R)-7-Benzoylamino-3-methylene-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]octane-2-carboxylic acid benzhydryl ester 

Downstream Products

• 68402-51-7 (6R,7R)-7-Benzoylamino-3-chloromethyl-7-methoxy-8-oxo-5-oxa-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester 

Relevant academic research and scientific papers

Preparation method of 3-chloromethyl oxacephem antibiotics parent nucleus

The invention discloses a preparation method of 3-chloromethyl oxacephem antibiotics parent nucleus and belongs to the technical field of drug synthesis. According to the invention, compound 1 is used as the raw material, and a three-step reaction is carr

New route to 3-(substituted) methyl 1-oxa- and (1-thia)cephems from 3-exomethylene intermediates via sulfenyl chloride adducts

Addition of methane- and benzenesulfenyl chlorides to 3-exomethylene-1-oxacephams 10 and 14 gave 3β-sulfenyl-3α-chloromethyl adducts 11 and 15. Nucleophilic substitution of the adducts proceeded facilely to afford compounds 18-23, which were converted into Δ3-dervatives 26 and 27 by oxidative elimination. This new route, as illustrated by the sequence 6 → 7 → 8 → 3, has an essential advantage in using the saturated intermediated 7 and 8 with a stabler β-lactam ring which is compatible in nucleophilic substitution, alkaline ester hydrolysis and further manipulations. These synthetic features are well demonstrated by successful synthesis of 1-oxacefamandol 35 and 7β-(2-thienylacetyl-amino)-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-ceph em-4-carboxylic acid (45).

CONVENIENT SYNTHESIS OF 3'-SUBSTITUTED METHYL 7α-METHOXY-1-OXACEPHEMS

A convenient synthesis of the title compounds 1 is achieved by formation of glycols 3, 12, 13 and 14 or chlorohydrins 6 from epioxazolines having pertinent allylic substituents, followed by stereoselective, intramolecular etherification to 4, 7, 15, 16 an

STEREOCONTROLLED, STRAIGHTFORWARD SYNTHESIS OF 3-SUBSTITUTED METHYL 7α-METHOXY-1-OXACEPHEMS

Stereocontrolled and industrially feasible synthesis of a new antibiotic 1a and related derivates, which is characterized by using all the carbon atoms of the penicillin skeleton, is described.