Chiral phosphoramidite auxiliaries and methods of their use
AssigneeSirius Therapeutics, Inc.
InventorsSukumar Sakamuri, Curt W. Bradshaw, Dingguo Liu, Laxman Eltepu
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Abstract
Disclosed are P-stereogenic groups that may be used in the synthesis of compounds including stereochemically enriched P-stereogenic phosphorothioates. P-stereogenic groups may be provided in nucleoside phosphoramidites including a sugar bonded to a nucleobase and to a stereochemically enriched phosphoramidite as well as methods of their use and methods of making them.
Claims13
A method of preparing a composition comprising a nucleoside phosphoramidite, the method comprising coupling an oxazaphospholane with a nucleoside, wherein the nucleoside phosphoramidite is of the following structure:
- wherein
- B1 is a nucleobase;
- Y1 is H or C1-6 alkyl;
- is a single carbon-carbon bond or a double carbon-carbon bond;
- each of R1 and R2 is independently an optionally substituted C1-6 alkyl or optionally substituted C6-10 aryl, or R1 and R2, together with the atoms to which each is attached, combine to form an optionally substituted C6-10 aryl;
- and
- each of R3 and R4 is H;
- R5 is H, O-protected hydroxyl, optionally substituted C1-6 alkoxy, or halogen;
- and
- R6 is a hydroxyl protecting group,
- wherein the oxazaphospholane has a structure of Formula (VIIIA) or (VIIIB),
- wherein X is halogen or pseudohalogen.
Dependencies are inferred from the claim text.