ISSN:
0170-2041
Keywords:
β-Sultam, 4-acyl-, 4-(α-hydroxylalkyl)-
;
1,2-Thiazetidine 1,1-dioxides
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Acylation of N-silylated and 2,3-substituted 1,2-thiazetidine 1,1-dioxides (β-sultams) results in the formation of 4-acylated β-sultams 2 and 8. The desilylation of 2 to 3 is easily done with TBAF either on silica gel or in ethanolic solution. The acylated β-sultams are reduced by sodium borohydride yielding α-hydroxyalkyl β-sultams 11 and 12, obtained as mixtures of diastereoisomers. These are separated by CC. The stereochemistry of the acylated and of the α-hydroxylated β-sultams is elucidated by spectroscopic methods, and compared to that of the antibiotic drug thienamycin.
Additional Material:
3 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199119910131
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