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US 2006/0135465 A1Published application
Synthesis and use of 2'-substituted-n6-modified nucleosides
AssigneeValeant Research & Development
InventorsHaoyun An, Kanda Ramasamy, Stephanie Shaw
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Abstract
An improved method of preparing a sugar modified nucleoside analog includes a protocol in which a hydroxy group of a sugar is selectively deprotected and oxidized prior to nucleophilic modification of the corresponding carbonyl group. The modified sugar is then coupled to a heterocyclic base that is modified with a dual nucleophilic reagent in a further step that provides N6-modified adenosine analogs with high stereoselectivity.
Claims17
A method of synthesizing an N6-substituted adenosine analog, comprising:
- providing a dual nucleophilic reagent having a first nucleophilic group and a second nucleophilic group, and an adenosine analog having a leaving group in the 6-position;
- reacting the dual nucleophilic reagent with the adenosine under a reaction condition such that the leaving group is replaced by the first nucleophilic group with a selectivity of at least 90%;
- and
- wherein the reaction condition comprises reaction in a non-basic environment under a protective atmosphere and a temperature of at least 40° C.
1 more element
A compound having a structure according to Formula I
- wherein R is selected from the group consisting of NHNH2, N(CH3)NH2, N(CH2CH3)NH2, N(CH3)OH, NHOH, NHOCH3, NHOCH2CH3, NHN(CH3)2, N(CH3)NHCH3, NHNHCH3, NHNHOCH3, and NHNHCOOCH3.
Dependencies are inferred from the claim text.