4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylicacid, 6-[(1R)-1-hydroxyethyl]-7-oxo-, 2-propen-1-yl ester, (5S,6S)-

Base Information

• Chemical Name: 4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylicacid, 6-[(1R)-1-hydroxyethyl]-7-oxo-, 2-propen-1-yl ester, (5S,6S)-
• CAS No.: 158250-71-6
• Molecular Formula: C11H13 N O4 S
• Molecular Weight: 255.295
• Mol file: 158250-71-6.mol

Synonyms:4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylicacid, 6-(1-hydroxyethyl)-7-oxo-, 2-propenyl ester, [5S-[5a,6b(S*)]]-;4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid,6-[(1R)-1-hydroxyethyl]-7-oxo-, 2-propenyl ester, (5S,6S)- (9CI); SB 213883

Chemical Property of 4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylicacid, 6-[(1R)-1-hydroxyethyl]-7-oxo-, 2-propen-1-yl ester, (5S,6S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylicacid, 6-[(1R)-1-hydroxyethyl]-7-oxo-, 2-propen-1-yl ester, (5S,6S)-

There total 1 articles about 4-Thia-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylicacid, 6-[(1R)-1-hydroxyethyl]-7-oxo-, 2-propen-1-yl ester, (5S,6S)- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(5S,6S)-3-Ethylsulfanyl-7-oxo-6-[(R)-1-(2,2,2-trichloro-ethoxycarbonyloxy)-ethyl]-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester (80629-49-8) → allyl (5S,6S,1'R)-6-(1'-hydroxyethyl)penem-3-carboxylate (158250-71-6) + allyl 6S-(1R-1-hydroxyethyl)2-ethylthio-2-penem-3-carboxylate (76431-43-1,76431-44-2,76431-50-0,76496-44-1,89395-53-9)

Guidance literature:

With zinc;

DOI:10.1016/S0040-4039(01)81938-9

Reference yield: 100.0%

allyl (5S,6S,1'R)-6-(1'-hydroxyethyl)penem-3-carboxylate (158250-71-6) + 3,4-di(tert-butyldiphenylsilyloxy)phenylacetic acid (182414-76-2) → (5S,6S)-6-((R)-1-{2-[3,4-Bis-(tert-butyl-diphenyl-silanyloxy)-phenyl]-acetoxy}-ethyl)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester (182414-66-0)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; 1.) -15 deg C, 20 min, 2.) 0 deg C, 30 min;

DOI:10.7164/antibiotics.49.921

Reference yield: 90.0%

allyl (5S,6S,1'R)-6-(1'-hydroxyethyl)penem-3-carboxylate (158250-71-6) + p-Nitrobenzyl monoester of succinic acid (79581-93-4) → Succinic acid (R)-1-((5S,6S)-2-allyloxycarbonyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-en-6-yl)-ethyl ester 4-nitro-benzyl ester (182414-61-5)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; 1.) -15 deg C, 20 min, 2.) 0 deg C, 30 min;

DOI:10.7164/antibiotics.49.921

upstream raw materials:

(5S,6S)-3-Ethylsulfanyl-7-oxo-6-[(R)-1-(2,2,2-trichloro-ethoxycarbonyloxy)-ethyl]-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester

Downstream raw materials:

(5S,6S)-6-{(R)-1-[2-(tert-Butyl-diphenyl-silanyloxy)-acetoxy]-ethyl}-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester

Succinic acid (R)-1-((5S,6S)-2-allyloxycarbonyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-en-6-yl)-ethyl ester 4-nitro-benzyl ester

(5S,6S)-6-{(R)-1-[3,4-Bis-(tert-butyl-diphenyl-silanyloxy)-benzoyloxy]-ethyl}-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester

(5S,6S)-6-((R)-1-{2-[3,4-Bis-(tert-butyl-diphenyl-silanyloxy)-phenyl]-acetoxy}-ethyl)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid allyl ester