81474-37-5

Basic information

• Product Name: (5R,6S)-6-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-tert-butylsulfanylmethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester
• CAS NO: 81474-37-5
• Molecular Weight: 566.815
• Mol File: 81474-37-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (5R,6S)-6-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-tert-butylsulfanylmethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (5R,6S)-6-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-tert-butylsulfanylmethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester(81474-37-5)
• EPA Substance Registry System: (5R,6S)-6-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-tert-butylsulfanylmethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester(81474-37-5)

Safety Data

• Hazardous Substances Data: 81474-37-5(Hazardous Substances Data)

Upstream product

• 78902-67-7 2-{(2R,3R)-2-Acetoxy-3-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-1-yl}-3-methyl-but-2-enoic acid methyl ester 
• 81474-34-2 [(2R,3S)-3-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-(2-tert-butylsulfanyl-acetylsulfanyl)-4-oxo-azetidin-1-yl]-hydroxy-acetic acid 4-nitro-benzyl ester 
• 81315-44-8 2-{3-Bromo-3-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-2-methylsulfanyl-4-oxo-azetidin-1-yl}-3-methyl-but-2-enoic acid methyl ester 
• 81474-36-4 tert-Butylsulfanyl-thioacetic acid S-{(2S,3R)-3-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl} ester 
• 81519-53-1 2-[3-Bromo-3-(1-hydroxy-ethyl)-2-methylsulfanyl-4-oxo-azetidin-1-yl]-3-methyl-but-2-enoic acid methyl ester 
• 76855-69-1 4-Acetoxy-3-<1-(t-butyldimethylsiloxy)ethyl>-2-azetidinone 
• 64370-35-0 p-nitrobenzyl glyoxylate 
• 78902-66-6 2-{(2R,3R)-3-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-methylsulfanyl-4-oxo-azetidin-1-yl}-3-methyl-but-2-enoic acid methyl ester 
• 78902-66-6 2-{(2R,3S)-3-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-methylsulfanyl-4-oxo-azetidin-1-yl}-3-methyl-but-2-enoic acid methyl ester 

Downstream Products

• 81474-39-7 p-nitrobenzyl (6,1')erythro-5,6-trans-6-(1'-t-butyldimethylsilyloxyethyl)-2-oxo-penam-3-carboxylate 
• 81474-38-6 (2S,5R,6S)-6-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-[1-tert-butylsulfanyl-meth-(E)-ylidene]-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester 

Relevant articles and documents

FROM PENICILLIN TO PENEM AND CARBAPENEM. 1. RACEMIZATION OF 6,6-DIBROMO SECOPENICILLIN, AND SYNTHESIS OF 2-OXO PENAM DERIVATIVE

From 6-APA the azetidinone derivative (7) which has (R)-hydroxyethyl substituent at C-6 was prepared effectively.From dibromoseco derivative (10) the same type of compounds, 17 and 18 which has (S) type substituent were prepared, however these were proved to be optically inactive dl-form.Racemization occurred during the proces of the formation of the secopenicillin (10) with excess CH3I and 2.5 eq. of NaH or KO-t-Bu in THF via the acyliminium intermediate (22).The 2-oxo penam derivative (27) was prepared from 17 as shown in Fig. 4.