357341-53-8

Upstream product

• 93711-85-4 (2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionic acid 
• 246519-26-6 2,5-anhydro-1-[[[(4-nitrophenyl)methoxy]carbonyl]-L-valyl]amino-1,4-dideoxy-3-thio-D-threo-pentitol 
• 161855-96-5 (S)-[1-[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl-2-methylpropyl]carbamic acid (4-nitrophenyl)methyl ester 

Downstream Products

• 357341-54-9 {3-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-[1-(2-{[3-methyl-2-(4-nitro-benzyloxycarbonylamino)-butyrylamino]-methyl}-tetrahydro-furan-3-ylsulfanylcarbonyl)-ethyl]-4-oxo-azetidin-1-yl}-oxo-acetic acid 4-nitro-benzyl ester 
• 161856-02-6 OCA 983 
• 246519-28-8 [1(S),3[4R,5S,6S(R)]]-1-[[[[2-(4-nitrophenyl)methoxy]carbonyl]amino-3-methyl-1-oxobutyl]amino]-2,5-anhydro-3-S-[6-(1-hydroxyethyl)-4-methyl-2-[[(4-nitrophenyl)methoxy]carbonyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-en-3-yl]-1,4-dideoxy-3-thio-D-threo-pentitol 
• 357341-55-0 (1R,5S,6S)-6-[(R)-1-(tert-butyldimethylsilanyloxyl)ethyl]-2-[[(2R,3R)-2-[[[(S)-2-(4-nitrobenzyloxycarbonyl)amino-3-methyl-1-oxobutyl]amino]methyl]tetrahydro-3-furanyl]thio]-1-methylcarbapen-2-em-3-carboxylic acid 4-nitrobenzyl ester 

Relevant academic research and scientific papers

Efficient synthesis of oral THF 1β-methylcarbapenem (OCA-983) via the Wittig process

An efficient and reproducible synthesis of orally active 2-tetrahydrofuranylthio-1β-methylcarbapenem 16 (OCA-983) via the Wittig process was developed. The intramolecular reductive cyclization of the thioester-oxalimide 13 with triethyl phosphite to the 2-tetrahydrofuranylthio-1β-methylcarbapenem 14 was carried out in two steps in order to obtain a reproducible yield.