148016-90-4

Upstream product

• 124-63-0 methanesulfonyl chloride 
• 148016-89-1 (2S,4S)-1-p-methoxybenzyloxycarbonyl-4-tritylthiopyrrolidine-2-methanol 
• 51-35-4 4R-4-hydroxyproline 
• 148016-88-0 (2S,4S)-1-p-methoxybenzyloxycarbonyl-4-tritylthiopyrrolidine-2-carboxylic acid methyl ester 
• 148016-87-9 (2S,4R)-1-p-methoxybenzyloxycarbonyl-4-methanesulfonyloxypyrrolidine-2-carboxylic acid methyl ester 
• 104773-44-6 (2S,4R)-1-p-methoxybenzyloxycarbonyl-4-hydroxypyrrolidine-2-carboxylic acid methyl ester 
• 1499-56-5 (R)-4-hydroxy-L-proline ethyl ester 

Downstream Products

• 175846-13-6 (2S,4S)-2-(2,4-Dioxo-imidazolidin-1-ylmethyl)-4-tritylsulfanyl-pyrrolidine-1-carboxylic acid 4-methoxy-benzyl ester 
• 148016-91-5 (2S,4S)-1-p-methoxybenzyloxycarbonyl-2-azidomethyl-4-tritylthiopyrrolidine 
• 148017-60-1 (1R,5S,6S)-2-[(3S,5S)-5-(1,1-dioxo-2-p-methoxybenzyloxycarbonyl-3,4,5,6-tetrahydro-1,2,6-thiadiazin-6-yl)methyl-1-p-methoxybenzyloxycarbonylpyrrolidin-3-yl]thio-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carba-2-penem-3-carboxylic acid p-methoxybenzyl ester 
• 148017-59-8 (1R,5S,6S)-2-[(3S,5S)-5-(1,1-dioxo-2-p-methoxybenzyloxycarbonyl-1,2,5-thiadiazolidin-5-yl)methyl-1-p-methoxybenzyloxycarbonylpyrrolidin-3-yl]thio-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carba-2-penem-3-carboxylic acid p-methoxybenzylester 
• 148017-54-3 C₄₁H₄₈N₄O₁₃S₂ 
• 175846-25-0 (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-3-{(3S,5S)-1-(4-methoxy-benzyloxycarbonyl)-5-[(4-methoxy-benzyloxycarbonylamino)-methyl]-pyrrolidin-3-ylsulfanyl}-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-methoxy-benzyl ester 
• 175846-37-4 (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-3-{(3S,5S)-1-(4-methoxy-benzyloxycarbonyl)-5-[(morpholine-4-sulfonylamino)-methyl]-pyrrolidin-3-ylsulfanyl}-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-methoxy-benzyl ester 
• 148017-58-7 C₃₄H₄₄N₄O₁₁S₂ 
• 175846-35-2 (4R,5S,6S)-3-[(3S,5S)-5-(Carbamoylmethanesulfonylamino-methyl)-1-(4-methoxy-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-methoxy-benzyl ester 
• 175846-36-3 (4R,5S,6S)-3-[(3S,5S)-5-[(2-Hydroxy-ethanesulfonylamino)-methyl]-1-(4-methoxy-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-methoxy-benzyl ester 
• 148016-96-0 (2S,4S)-1-p-methoxybenzyloxycarbonyl-4tritylthio-2-(p-methoxybenzyloxycarbonylaminosulfonylaminomethyl)pyrrolidine 
• 175846-30-7 C₃₄H₄₂N₄O₁₀S 
• 175846-31-8 (4R,5S,6S)-3-[(3S,5S)-5-(2,4-Dioxo-imidazolidin-1-ylmethyl)-1-(4-methoxy-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-methoxy-benzyl ester 
• 175846-28-3 (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-3-((3S,5S)-1-(4-methoxy-benzyloxycarbonyl)-5-{[(pyridine-3-carbonyl)-amino]-methyl}-pyrrolidin-3-ylsulfanyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-methoxy-benzyl ester 

Relevant academic research and scientific papers

A novel 1β-methylcarbapenem antibiotic, S-4661 synthesis and structure-activity relationships of 2-(5-substituted pyrrolidin-3-ylthio)-1β-methylcarbapenems

The synthesis and biological activity of (1R,5S,6S)-2-[(3S,5S)-5-substituted pyrrolidin-3-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acids are described. These compounds exhibit potent antibacterial activity against a wide range of both Gram-positive and Gram-negative bacteria including Pseudomonas aeruginosa. Of these new carbapenems, (1R,5S,6S)-2-[(3S,5S)-5-sulfamoylaminomethyl pyrrolidin-3-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid (S-4661) showed the most potent and well balanced activity and was selected as a candidate for further evaluation.

Pyrrolidylthiocarbapenem derivative

A pyrrolidylthiocarbapenem derivative represented by Formula I is provided: STR1 wherein R1 is hydrogen or lower alkyl; R2, R3 and R4 are hydrogen, lower alkyl which can be substituted or an amino protecting group independently, or R2 and R3 together with a nitrogen atom to which R2 and R3 are bonded form a saturated or unsaturated cyclic group, or R2 and R4, or R3 and R4 together with two nitrogen atoms and one sulfur atom in the sufamide group form a saturated or unsaturated cyclic group; each cyclic group can further include at least one atom selected from the group consisting of oxygen, sulfur and nitrogen, and each cyclic group can be substituted; X1 is hydrogen or a hydroxy protecting group; X2 is hydrogen, a carboxy protecting group, an ammonio group, an alkali metal or an alkaline-earth metal; and Y2 is hydrogen or an amino protecting group.