Method for production of nucleoside derivatives by selective hydrolysis
AssigneeAjinomoto Co., Inc.
InventorsHiroshi Shiragami, Yasuhiro Tanaka, Hisao Iwagami
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Abstract
A method for selective hydrolysis of nucleoside derivatives using cyclodextrin in basic solution is disclosed.
Claims32
A process for production of a nucleoside represented by the structure of formula (III) or (IV) which comprises selectively hydrolyzing a nucleoside compound represented by the structure of formula (I) or (II) in the presence of a cyclodextrin and an inorganic base to selectively convert said compound into a nucleoside compound (III) or (IV);
- ##STR11## wherein:
- B:
- a nucleoside base
- R.sup.1, R.sup.2 :
- a hydrolyzable acyl group having 1 to 12 carbon atoms;
- R.sup.3 :
- a hydrolyzable acyl group having 1 to 12 carbon atoms or hydrogen;
- and,
- X:
- a hydrogen atom, a halogen atom, an alkyl group having 1 to 12 carbon atoms or an acyloxy group having 1 to 12 carbon atoms.
The process wherein X is a member selected from the group consisting of fluorine, chlorine, bromine and iodine.
A process for the production of a dideoxynucleoside compound represented by the structure of formula (IX) ##STR12## comprising:
- (i) selectively hydrolyzing a nucleoside compound represented by the structure of formula (I) or (II) in the presence of a cyclodextrin and an inorganic base to selectively convert said compound into a nucleoside compound represented by the structure of formula (III) or (IV);
- ##STR13## wherein:
- B:
- a nucleoside base
- R.sup.1, R.sup.2 :
- a hydrolyzable acyl group having 1 to 12 carbon atoms;
- R.sup.3 :
- a hydrolyzable acyl group having 1 to 12 carbon atoms or hydrogen;
- and,
- X:
- a hydrogen atom, a halogen atom, an alkyl group having 1 to 12 carbon atoms or an acyloxy group having 1 to 12 carbon atoms;
- (ii) converting the hydroxyl groups of said nucleoside compound (III) or (IV) into a group capable of being replaced by hydrogen and,
- (iii) subjecting said nucleoside compound to hydrogenation.
A process for the production of a nucleoside compound represented by the structure of formula (V) or (VI):
- ##STR14## wherein B is a nucleoside base and R.sup.1 is a hydrolyzable acyl group having 1 to 12 carbon atoms comprising:
- (i) selectively hydrolyzing a nucleoside compound represented by the structure of formula (I) or (II) in the presence of a cyclodextrin and an inorganic base to selectively convert said compound into a nucleoside compound represented by the structure of formula (III) or (IV);
- ##STR15## wherein:
- B:
- a nucleoside base
- R.sup.1, R.sup.2 :
- a hydrolyzable acyl group having 1 to 12 carbon atoms;
- R.sup.3 :
- a hydrolyzable acyl group having 1 to 12 carbon atoms or hydrogen;
- and
- X:
- a hydrogen atom or a halogen atom;
- (ii) subjecting said nucleoside (III) wherein X is a halogen or (IV) wherein X is a halogen to hydrogenation.
A process for the production of a nucleoside compound represented by the structure of formula (VII) or (VIII):
- ##STR16## wherein B is a nucleoside base and R.sup.3 represents a hydrolyzable acyl group having 1 to 12 carbon atoms or hydrogen comprising:
- (i) selectively hydrolyzing a nucleoside compound represented by the structure of formula (I) or (II) in the presence of a cyclodextrin and an inorganic base to selectively convert said compound into a nucleoside compound represented by the structure of formula (III) or (IV);
- ##STR17## wherein:
- B:
- a nucleoside base
- R.sup.1, R.sup.2 :
- a hydrolyzable acyl group having 1 to 12 carbon atoms;
- R.sup.3 :
- a hydrolyzable acyl group having 1 to 12 carbon atoms or hydrogen;
- and
- X:
- a hydrogen atom or a halogen atom;
- (ii) subjecting said nucleoside compound (III) wherein X is a halogen or (IV) wherein X is a halogen to hydrogenation to produce a nucleoside compound represented by the structure of formula (V) or (VI) ##STR18## (iii) and further reacting said nucleoside compound (V) or (VI) with a fluorinating agent.
Dependencies are inferred from the claim text.