88669-72-1

Upstream product

• 13616-37-0 ethyl (tetrazol-5-yl)acetate 
• 100-39-0 benzyl bromide 
• 100-44-7 benzyl chloride 

Downstream Products

• 88669-99-2 {2-[(5R,6S)-2-(1-Benzyl-1H-tetrazol-5-yl)-6-((R)-1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-3-ylsulfanyl]-ethyl}-carbamic acid 4-nitro-benzyl ester 
• 88669-91-4 Phosphoric acid (5R,6S)-2-(1-benzyl-1H-tetrazol-5-yl)-6-((R)-1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-3-yl ester diphenyl ester 
• 88669-92-5 (5R,6S)-2-(1-Benzyl-1H-tetrazol-5-yl)-6-((R)-1-hydroxy-ethyl)-3-phenylsulfanyl-1-aza-bicyclo[3.2.0]hept-2-en-7-one 
• 88669-71-0 (3S,4R)-4-[3-(1-Benzyl-1H-tetrazol-5-yl)-2-oxo-propyl]-3-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-azetidin-2-one 
• 88669-96-9 (5R,6S)-2-(1-Benzyl-1H-tetrazol-5-yl)-3-ethylsulfanyl-6-((R)-1-hydroxy-ethyl)-1-aza-bicyclo[3.2.0]hept-2-en-7-one 
• 88669-86-7 (3S,4R)-4-[3-(1-Benzyl-1H-tetrazol-5-yl)-3-diazo-2-oxo-propyl]-3-((R)-1-hydroxy-ethyl)-azetidin-2-one 
• 88669-84-5 (3S,4R)-4-[3-(1-Benzyl-1H-tetrazol-5-yl)-2-oxo-propyl]-3-((R)-1-hydroxy-ethyl)-azetidin-2-one 
• 88669-88-9 (2S,5R,6S)-2-(1-Benzyl-1H-tetrazol-5-yl)-6-((R)-1-hydroxy-ethyl)-1-aza-bicyclo[3.2.0]heptane-3,7-dione 
• 64953-18-0 (1-benzyl-1H-tetrazol-5-yl)-acetic acid 

Relevant academic research and scientific papers

A reagent, ethyl 2-(2-tert-butyl-2H-tetrazol-5-yl)-3-(dimethylamino)acrylate (DMTE), for facile synthesis of 2,3-(ring fused)-5-(5-tetrazolyl)-4H-pyrimidin-4-one derivatives

A method for synthesizing 2,3-(ring fused)-5-(5-tetrazolyl)-4H-pyrimidin-4-one derivatives from ethyl 2-(2-tert-butyl-2H-tetrazol-5-yl)-3-(dimethylamino)acrylate (DMTE) (4a) and amino-heterocycles is described. The structure of DMTE, which was prepared from ethyl (2-tert-butyl-2H-tetrazol-5-yl)acetate (3a) with dimethylformamide diethylacetal, was determined by X-ray analysis to be Z form. The reaction of 2-amino-5-methyloxazole (6) with DMTE in acetic acid gave the oxazolo[3,2-a]pyrimidine derivative (8), heating of which in concentrated sulfuric acid afforded the desired tetrazole derivative (20). Pyrimido[2,1-b]benzothiazole (21), pyrazolo[1,5-a]pyrimidine (22 and 23) and [1,2,4]triazolo[1,5-a]pyrimidine (24) derivatives were prepared in a similar manner.

Total Synthesis of 3-(5-Tetrazolyl)carbapenems

The synthesis of the title compounds, β-lactam antibiotics, is described.A new tetrazole protecting group, (((p-nitrobenzyl)carbonyl)oxy)methyl, was succesfully applied.Substitution of carboxyl by tetrazole on the carbapenem nucleus results in stability to a degradative renal enzyme.