Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 8, Issue 24, Pages 5505-5510Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c0ob00104j
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- Polish Ministry of Science and Higher Education [3 T09A 059 28]
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A new method for the formation of organohypophosphates containing a P-P bond under mild conditions, based on the DBU-assisted reaction of 2-alkoxy-2-thio-1,3,2-oxathiaphospholanes with O,O-dialkyl H-phosphonates or H-thiophosphonates, has been elaborated. The resulting triesters of P-1-thio- and P-1, P-2-dithiohypophosphoric acids, respectively, having O-methyl or O-ethyl groups, can be selectively dealkylated to form the corresponding di- or monoesters. Appropriately protected 2'-deoxyguanosine-3'-O-(2-thio-1,3,2-oxathiaphospholane) was converted into the corresponding P-1-thio- and P-1, P-2-dithiohypophosphate esters in a highly stereoselective manner (98%+ and 90%+, respectively).
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