Open Accessα‐ d ‐Glucofuranose and α‐ d ‐allofuranose diacetonides and silyl ether of α‐ d ‐glucofuranose diacetonide in dithiophosphorylation reactions
Author(s) -
Nizamov Ilyas S.,
Nikitin Yevgeniy N.,
Nizamov Ilnar D.,
Belov Timur G.,
Voloshina Alexandra D.,
Batyeva Elvira S.,
Cherkasov Rafael A.
Publication year - 2016
Publication title -
heteroatom chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.283
H-Index - 42
eISSN - 1098-1071
pISSN - 1042-7163
DOI - 10.1002/hc.21344
Subject(s) - chemistry , silyl ether , yield (engineering) , silylation , ether , disulfide bond , staphylococcus aureus , ammonium , medicinal chemistry , organic chemistry , bacteria , catalysis , biochemistry , biology , metallurgy , genetics , materials science
α‐ d ‐Glucofuranose and α‐ d ‐allofuranose diacetonides react with 2,4‐diorganyl 1,3,2,4‐dithiadiphosphetane‐2,4‐disulfides to form optically active dithiophosphonates in 78–81% yields, which are transformed into the corresponding ammonium salts in 90–97% yields by the treatment of n ‐hexadecylamine. The S ‐silyldithiophosphonate was prepared in 93% yield by the reaction of 2,4‐bis(butoxyphenyl) 1,3,2,4‐dithiadiphosphetane‐2,4‐disulfide with silyl ether of α‐ d ‐glucofuranose diacetonide. One of the salts obtained possesses antibacterial activity against Staphylococcus aureus ATCC 6538‐P.