Direct Mitsunobu monoesterification of N-protected tobramycin competes with intramolecular pyrrolidine formation in ester prodrug synthesis
Author(s)
Quader, Sabina
Boyd, Sue E
Jenkins, Ian D
Houston, Todd A
Year published
2015
Metadata
Show full item recordAbstract
Unlike the related aminoglycoside neomycin B, N-protected tobramycin can be selectively esterified at its sole, primary hydroxyl group under Mitsunobu conditions. However, depending on the reaction conditions, the reaction can take a different course with intramolecular cyclization of an N-Boc amine leading to formation of an unusual tobramycin pyrrolidine derivative as the major reaction product.Unlike the related aminoglycoside neomycin B, N-protected tobramycin can be selectively esterified at its sole, primary hydroxyl group under Mitsunobu conditions. However, depending on the reaction conditions, the reaction can take a different course with intramolecular cyclization of an N-Boc amine leading to formation of an unusual tobramycin pyrrolidine derivative as the major reaction product.
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Journal Title
Carbohydrate Research
Volume
413
Subject
Medicinal and biomolecular chemistry
Biologically active molecules
Organic chemistry
Organic chemical synthesis
Biochemistry and cell biology