180335-90-4Relevant academic research and scientific papers
Straightforward synthesis of lipophilic thymidine glucopyranosyl monophosphates as models for a drug delivery system across cellular membranes
Belsito, Emilia,Liguori, Angelo,Napoli, Anna,Siciliano, Carlo,Sindona, Giovanni
, p. 2565 - 2580 (2007/10/03)
O-methyl (3'-6) and (5'-6) thymidinyl gluco- and mannopyranosides and (3'-6) thymidinyl glucofuranose can be synthesised in excellent yields by applying the phosphotriester method. The lipophilic phosphotriesters thus obtained are designed as carriers of nucleoside drugs across cellular membranes.
A novel approach to the synthesis of lipophilic thymidinemonophosphoglucopyranosides as drug delivery systems
De Nino, Antonio,Liguori, Angelo,Procopio, Antonio,Roberti, Edoardo,Sindona, Giovanni
, p. 77 - 86 (2007/10/03)
The paper describes the synthesis of the hexadecyl phosphotriesters of thymidine 3′-(5′-deoxythymidin-5′-yl phosphate), thymidine 5′-(5′-deoxythymidin-5′-yl phosphate), thymidine 5′-(3′,5′-dideoxythymidin-5′-yl phosphate), thymidine 3′-[(methyl 6-deoxy-α-D-glucopyranosid-6-yl) phosphate], and thymidine 5′-[(methyl 6-deoxy-α-D-glucopyranosid-6-yl) phosphate]. The novel approach is based on the condensation of unprotected nucleosides or pyranosides with the lipophilic phosphodiesters 5′-O-dimethoxytritylthymidine 3′-(hexadecyl phosphate) and 3′-O-dimethoxytritylthymidine 5′-(hexadecyl phosphate) which were obtained in satisfactory yield from hexadecyl phosphorodichloridite and 5′-O-dimethoxytrityl-or 3′-dimethoxytrityl-thymidine. The latter was prepared in high yield from 5′-O-(4-nitrobenzoyl)thymidine, obtained from thymidine, 4-nitrobenzoic acid, and bis(2-oxooxazolidin-3-yl)phosphinic chloride, by a one-pot procedure. The introduction of the aliphatic chain in the early stage of the synthesis prevents the alkylation of the nucleobases and allows a regioselective phosphorylation of unprotected nucleosides and pyranosides.
