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Synthesis of Pyranonucleoside‐6′‐triphosphates through the cyclo Sal‐Method
Author(s) -
Huchting Johanna,
Meier Chris
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402047
Subject(s) - chemistry , silylation , pyrophosphate , protecting group , regioselectivity , titration , ion exchange , phosphate , chemical synthesis , chromatography , ion exchange resin , combinatorial chemistry , organic chemistry , catalysis , ion , biochemistry , alkyl , in vitro , enzyme
The high yielding synthesis of pyranonucleoside‐6′‐triphosphates by using the cyclo Sal‐method is described. Synthesis of the activated cyclo Sal‐pyranonucleoside‐6′‐phosphate triesters was achieved by applying a synthetic route that had been developed for the synthesis of cyclo Sal‐(glycopyranosyl‐6)‐phosphates by us. The route involved regioselective 6′‐ tert ‐butyldimethylsilyl protection and exchange of the silyl protecting group by the fluorenylmethyloxycarbonyl (Fmoc) group. The 6′‐Fmoc‐protected derivatives were selectively converted into the cyclo Sal‐triester. These were then very efficiently converted into triphosphates by a “titration‐like” reaction with pyrophosphate. Simple purification by first ion exchange followed by reversed phase (RP) column chromatography afforded the triphosphates in very good yields.