Synthesis of a C3 Hydroxyproline-modified Carbapenem

Methyl (4 R )-4-hydroxy-1-(sulfanylacetyl)-l-prolinate was synthesized starting from trans -4-l-hydroxyprolinate methyl ester hydrochloride and then reacted with the known carbapenem enol phosphate to obtain the corresponding carbapenem and then to chemically more stable methyl ester.

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Bibliographic Details
Published inRussian journal of organic chemistry Vol. 58; no. 11; pp. 1664 - 1667
Main Authors Valiullina, Z. R., Galeeva, A. M., Miftakhov, M. S.
Format Journal Article
LanguageEnglish
Published Moscow Pleiades Publishing 2022
Springer Nature B.V
Subjects
Chemistry
Chemistry and Materials Science
Organic Chemistry
β-lactam antibiotics
4-l-hydroxyproline
carbapenems
carbapenemenol phosphate
2-ethoxythiolanone
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Summary:Methyl (4 R )-4-hydroxy-1-(sulfanylacetyl)-l-prolinate was synthesized starting from trans -4-l-hydroxyprolinate methyl ester hydrochloride and then reacted with the known carbapenem enol phosphate to obtain the corresponding carbapenem and then to chemically more stable methyl ester.
ISSN:1070-4280
1608-3393
DOI:10.1134/S1070428022110173