Glycoside compound, amidite compound, and production method for polynucleotide using said compounds
AssigneeSumitomo Chemical Company, Limited
InventorsIkuya Oshiro, Tatsuya Saito, Hideki Ihara
Life of this patent
Estimating the term…
Abstract
The present invention provides an amidite compound capable of improving a yield and a purity of a polyoligonucleotide, a glycoside compound as an intermediate thereof, and a production method for a polynucleotide using the amidite compound. The present invention also provides an amidite compound of formula (1) capable of improving a yield and a purity of a polyoligonucleotide, a glycoside compound of formula (10) (in formulae (10) and (1), Ba, Ra, Rb, Rc, G1, G2, and G3 are as defined in the description, and R is represented by the following formulae), and a production method for a polynucleotide using the amidite compound.
Claims21
An amidite compound represented by formula (1):
- wherein R represents a group represented by a formula:
- wherein:
- Ra and Rb are identical to or different from each other and each represents a methyl group, an ethyl group, or a hydrogen atom, provided that Ra and Rb do not represent a hydrogen atom at the same time;
- and
- Rc represents a phenyl group which may be substituted with a halogen atom, a methyl group, a nitro group, a methoxy group, or a trifluoromethyl group;
- a C1 to C10 alkyl group;
- or a benzyl group,
- Ba represents a group having an optionally-protected nucleobase structure,
- G1 and G2 are identical to or different from each other and each represents a protecting group of a hydroxyl group, and
- G3 is identical to or different from each other and each represents an alkyl group.
An ether compound represented by formula (4):
- wherein:
- Ra and Rb are identical to or different from each other and each represents a methyl group, an ethyl group, or a hydrogen atom, provided that Ra and Rb do not represent a hydrogen atom at the same time;
- Rc represents a phenyl group which may be substituted with a halogen atom, a methyl group, a nitro group, a methoxy group, or a trifluoromethyl group;
- a C1 to C10 alkyl group;
- or a benzyl group;
- and
- Rd represents C1 to C10 alkyl or a phenyl group.
A production method for an ether compound represented by formula (4), the method comprising step a of reacting a 2-hydroxyalkylsulfone represented by formula (5) with a bisthioether compound represented by formula (12) in a solvent in presence of a halogenating agent and an acid:
- wherein:
- Ra and Rb are identical to or different from each other and each represents a methyl group, an ethyl group, or a hydrogen atom, provided that Ra and Rb do not represent a hydrogen atom at the same time;
- and
- Rc represents a phenyl group which may be substituted with a halogen atom, a methyl group, a nitro group, a methoxy group, or a trifluoromethyl group;
- a C1 to C10 alkyl group;
- or a benzyl group,
- wherein Rd represents C1 to C10 alkyl or a phenyl group,
- wherein Ra, Rb, Rc, and Rd are as defined above.
A production method for a compound represented by formula (8), the method comprising reacting a compound represented by formula (7) with a compound represented by formula (4) in presence of a halogenating agent:
- wherein Ba represents a compound having an optionally-protected nucleobase structure, and G4 represents a protecting group of a hydroxyl group,
- wherein Ra and Rb are identical to or different from each other and each represents a methyl group, an ethyl group, or a hydrogen atom, provided that Ra and Rb do not represent a hydrogen atom at the same time,
- Rc represents a phenyl group which may be substituted with a halogen atom, a methyl group, a nitro group, a methoxy group, or a trifluoromethyl group;
- a C1 to C10 alkyl group;
- or a benzyl group, and
- Rd represents C1 to C10 alkyl or a phenyl group,
- wherein Ba, Ra, Rb, and Rc are as defined above, and G4 represents a protecting group of a hydroxyl group.
A compound represented by formula (8):
- wherein
- Ba represents a compound having an optionally-protected nucleobase structure,
- Ra and Rb are identical to or different from each other and each represents a methyl group, an ethyl group, or a hydrogen atom, provided that Ra and Rb do not represent a hydrogen atom at the same time,
- Rc represents a phenyl group which may be substituted with a halogen atom, a methyl group, a nitro group, a methoxy group, or a trifluoromethyl group;
- a C1 to C10 alkyl group;
- or a benzyl group, and
- G4 represents a protecting group of a hydroxyl group.
A compound represented by formula (9):
- wherein
- Ba represents a compound having an optionally-protected nucleobase structure,
- Ra and Rb are identical to or different from each other and each represents a methyl group, an ethyl group, or a hydrogen atom, provided that Ra and Rb do not represent a hydrogen atom at the same time,
- Rc represents a phenyl group which may be substituted with a halogen atom, a methyl group, a nitro group, a methoxy group, or a trifluoromethyl group;
- a C1 to C10 alkyl group;
- or a benzyl group.
A compound represented by formula (10):
- wherein
- Ba represents a compound having an optionally-protected nucleobase structure,
- Ra and Rb are identical to or different from each other and each represents a methyl group, an ethyl group, or a hydrogen atom, provided that Ra and Rb do not represent a hydrogen atom at the same time,
- Rc represents a phenyl group which may be substituted with a halogen atom, a methyl group, a nitro group, a methoxy group, or a trifluoromethyl group;
- a C1 to C10 alkyl group;
- or a benzyl group, and
- G1 represents a protecting group of a hydroxyl group.
Dependencies are inferred from the claim text.