Designing an effective approach for obtaining methylenecarboxylate analogues of adenophostin A. Preliminary results.
Preliminary results for the synthesis of two new adenophostin analogues incorporating 3''- and 4''-methylenecarboxylate surrogate groups are presented. The synthesis involves the preparation of 3''- and 4''-methylenecarboxylate glucose derivatives by a radical allylation-oxidative cleavage approach, their conversion into thioglycoside precursors, and stereoselective glycosylation of a suitable adenosine derivative. The glycosylations proceeded with excellent stereoselectivity, only the alpha product was detected, and in good yields.
Departament de Química Analítica i Química Orgànica, Facultat de Química, Universitat Rovira i Virgili, C/Marcel lí Domingo s/n, 43007 Tarragona, Spain.
David
D
Benito
M
M
Isabel Matheu
Alain
A
Morère
Yolanda
Y
Díaz
Sergio
S
Castillón
D000241:Adenosine / Q000031:analogs & derivatives* / Q000737:chemistry; D002120:Calcium Channel Agonists; D002264:Carboxylic Acids / Q000737:chemistry*; D005947:Glucose / Q000737:chemistry; D006031:Glycosylation
D002120:Calcium Channel Agonists; D002264:Carboxylic Acids; C085029:adenophostin A; D005947:Glucose; D000241:Adenosine