35353-33-4

Upstream product

• 62801-95-0 (2S,6S)-6-[Bis-(2,2,2-trichloro-ethoxy)-phosphorylamino]-6-methoxy-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester 
• 103-80-0 phenylacetyl chloride 
• 35353-32-3 6β-amino-6α-methoxy-penicillanic acid benzyl ester 
• 103-82-2 phenylacetic acid 
• 1555-80-2 phenylacetic anhydride 
• 35353-31-2 benzyl 6β-azido-6-methoxypenicillanate 
• 40514-98-5 (6S)-benzyl 6-amino-6-(methylthio)penicillanate 
• 41926-40-3 6β-benzylideneamino-6α-methoxy-penicillanic acid benzyl ester 
• 56915-14-1 benzyl 6α-methylthio-6β-phenylacetamidopenicillanate 
• 3956-31-8 (2S,6R)-6-Amino-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester 
• 75636-71-4 benzyl 6β-penicillanate 
• 86062-79-5 (2S,6S)-6-Methanesulfinyl-3,3-dimethyl-7-oxo-6-phenylacetylamino-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzyl ester 

Downstream Products

• 40400-92-8 6α-methoxy-6β-(2-phenyl-acetylamino)-penicillanic acid 

Relevant academic research and scientific papers

A Method for the Preparation of 7α-Methoxycephalosporins

A method for the preparation of 7α-methoxycephalosporins has been developed. 7β-Phosphoramidodeacetoxycephalosporin (6) and 7β-phosphoramidocephalosporin (14) obtained from the 7β-amino-derivatives (5) and (13), were converted into 7α-methoxy-7β-phosphoramidodeacetoxycephalosporin (7) and 7α-methoxy-7β-phosphoramidocephalosporin (15), respectively, by reaction with LiOMe and ButOCl.Treatment of (7) with BunLi and Et3N followed by acylation with phenylacetyl chloride gave 7α-methoxy-7β-phenylketenimino-derivative (11), which were easily hydrated to 7α-methoxy-7β-(phenylacetamido)deacetoxycephalosporin (12).Treatment of (15) under similar conditions afforded, contrary to the result obtained with (7), 7α-methoxy-7β-(phenylacetamido)cephalosporin (16), without any of the corresponding ketenimine.This method was also successfully applied to the synthesis of 6α-methoxypenicillins.

7β-Phosphoramido-7α-methoxycephalosporanic acid derivatives

Cephem and penam compounds having a partial structure of formula (II): STR1 wherein R1 and R2, respectively, represent a hydrocarbon group which is attached to P, either directly or through an oxygen atom, and which may optionally be substituted, and R3 is a hydrocarbon residue, are useful as intermediates for synthetic penicillins and cephalosporins, which in turn are useful as antibiotics or intermediates for some other synthetic penicillins and cephalosporins having antibiotic activity. To the 6- or 7-amino group of these penam or cephem compounds an objective acyl group can be introduced to give 6- or 7-acyl amino compound in a good yield, without isomerization of 6α-or 7α-substituent OR3 of the penam or cephem compounds.

Derivatives of 6-aminopenicillanic acid

Novel 6-methoxy and 6-thioalkyl-6-acylamidopenicillanic acids and their non-toxic pharmaceutically-acceptable salts, esters and amides which are useful as antibiotics. The products are prepared by treating an ester of 6-substituted-6-aminopenicillanic acid with an acylating agent followed by removal of the ester group. Also disclosed are novel intermediates.

6α, β-Substituted penicillin derivatives

Novel 6-methoxy and 6-thioalkyl-6-acylamido-penicillanic acids and their non-toxic pharmaceutically-acceptable salts, esters and amides which are useful as antibiotics. The products are prepared by treating an ester of 6-substituted-6-aminopenicillanic acid with an acylating agent followed by removal of the ester group. Also disclosed are novel intermediates.