Process for producing 1,2-trans-glycoside compound

1. A process for preparing a glycoside compound comprising a glycosidic bond that selectively forms a trans configuration relative to the C-2 hydroxyl group, the process comprising

reacting a furanose compound or a pyranose compound with an alcohol compound,

wherein the hydroxyl at the C-2 position of the furanose compound or the pyranose compound is protected with a group A,

wherein R 2 and R 3 are connected via an alkylene group having 2 to 4 carbon atoms, further wherein the alkylene group is optionally substituted with an alkyl group having 1 to 4 carbon atoms, or optionally comprises an intervening phenylene, and m and n are each an integer of 0 or 1; and the furanose compound or the pyranose compound optionally comprises a substituent.

2. The process of claim 1 , wherein the furanose compound is arabofuranose, erythrofuranose, glucofuranose, ribofuranose, threofuranose or xylofuranose; the pyranose compound is arabopyranose, altropyranose, glucopyranose, galactopyranose, glopyranose, mannopyranose, ribopyranose, xylopyranose or glucopyranuronic acid; and the alcohol compound is an aliphatic alcohol comprising 1 to 4 carbon atoms, alicyclic alcohol comprising 5 to 8 carbon atoms, aromatic alcohol, furanose, pyranose, aminopyranose, anhydrosugar, polysaccharide, N-acetylpyranose or glycerol.

3. A process for preparing a 2-phosphonoyl-1,2-transglycoside compound of formula (3) comprising reacting an alcohol compound of formula (2) with a 2-phosphonoylpyranose compound of formula (1), formula (1) comprising:

Q 1 -Z  (1)

wherein Q 1 =

Z is a group —S—R 1 , a group —SO—R 1 , a group —Se—R 1 , a group —O—C(═NH)CX 3 , a halogen atom, an alkoxyl, an alkenyloxy, a group —P(OR 1 ) 3 or a group —PO(OR 1 ) 3 , R 1 is an alkyl comprising 1 to 20 carbon atoms, an aryl optionally substituted or a heteroaromatic group, X is a halogen atom, R 4 , R 5 and R 6 are the same or different and are each a protective group for the saccharide hydroxyl group, E is methylene or a carbonyl, and A is

wherein R 2 and R 3 are connected via an alkylene group having 2 to 4 carbon atoms, further wherein the alkylene group is optionally substituted with an alkyl group having 1 to 4 carbon atoms, or optionally comprises an intervening phenylene, and m and n are each an integer of 0 or 1;

formula (2) comprising:

Q 2 -OH  (2)

wherein Q 2 is an alkyl having 1 to 4 carbon atoms, a cycloalkyl comprising 5 to 8 carbon atoms, optionally substituted, or one of the following groups

wherein L 1 is a group —OA 1 , —OG or —N(J 1 )(J 2 ), A 1 is a group shown below, G is a protective group for the saccharide hydroxyl, and J 1 and J 2 are each a hydrogen atom or a protective group for amino

R 2′ and R 3′ are combined with each other to form an alkylene having 2 or 4 carbon atoms, further, wherein the alkylene is optionally substituted with alkyl having 1 to 4 carbon atoms, or optionally comprises an intervening phenylene, m′ and n′ are each an integer of 0 or 1, Z 1 is a group —S—R 1′ , a group —SO—R 1′ , a group —Se—R 1′ , a group —O—C(═NH)CX′ 3 , a halogen atom, an alkoxyl, an alkenyloxy, a group —P(OR 1 ') 3 , a group —PO(OR 1′ ) 3 or —OG 1 , R 1′ is an alkyl comprising 1 to 20 carbon atoms, an aryl optionally substituted or a heteroaromatic group, X′ is a halogen atom, G 1 is a protective group for the saccharide hydroxyl, R 7 , R 8 and R 9 are the same or different and are each a protective group for the saccharide hydroxyl group, and E 1 is methylene or a carbonyl; and

formula (3) comprising:

Q 1a -O-Q 2   (3)

wherein Q 1a =

and Q 2 , A, R 4 , R 5 and R 6 are as defined above.

4. A process for preparing a 2-phosphonoyl-1,2-transglycoside compound of formula (3a) comprising reacting an alcohol compound of formula (2a) with a 2-phosphonoylpyranose compound of formula (1), formula (1) comprising:

Q 1 -Z  (1)

wherein Q 1 =

Z is a group —S—R 1 , a group —SO-R 1 , a group —Se—R 1 , a group —O-C(=NH)CX 3 , a halogen atom, an alkoxyl, an alkenyloxy, a group —P(OR 1 ) 3 or a group —PO(OR 1 ) 3 , R 1 is an alkyl comprising 1 to 20 carbon atoms, an aryl optionally substituted or a heteroaromatic group, X is a halogen atom, R 4 , R 5 and R 6 are the same or different and are each a protective group for the saccharide hydroxyl group, E is methylene or a carbonyl, and A is

wherein R 2 and R 3 are connected via an alkylene group having 2 to 4 carbon atoms, further wherein the alkylene group is optionally substituted with an alkyl group having 1 to 4 carbon atoms, or optionally comprises an intervening phenylene, and m and n are each an integer of 0 or 1;

formula (2a) comprising:

Q 2a -OH  (2a)

wherein Q 2a is one of the groups given below,

A 1 is

R 2′ and R 3′ are combined with each other to form an alkylene having 2 or 4 carbon atoms, further, wherein the alkylene is optionally substituted with alkyl having 1 to 4 carbon atoms, or optionally comprises an intervening phenylene, m′ and n′ are each an integer of 0 or 1;

R 7 , R 8 , R 9 are the same or different and are each a protective group for the saccharide hydroxyl group, and E 1 is methylene or carbonyl, Z 2 is a group —S—R 1′ , a group —SO—R 1′ , a group —Se—R 1′ , a group —O—C(═NH)CX' 3 , a halogen atom, an alkoxyl, an alkenyloxy, a group —P(OR 1′ ) 3 or a group —PO(OR 1′ ) 3 , R 1′ is an alkyl comprising 1 to 20 carbon atoms, an aryl optionally substituted, or a heteroaromatic group, and X is a halogen atom; and

formula (3a) comprising:

Q 1a -O-Q 2a   (3a)

wherein Q 1a =

R 4 , R 5 and R 6 are the same or different and are each a protective group for the saccharide hydroxyl group, E is methylene or a carbonyl, and A is

wherein R 2 and R 3 are connected via an alkylene group having 2 to 4 carbon atoms, further wherein the alkylene group is optionally substituted with an alkyl group having 1 to 4 carbon atoms, or optionally comprises an intervening phenylene, and m and n are each an integer of 0 or 1;

and Q 2a is as defined above.

5. A process for preparing a 2-phosphonoyl-1,2-transglycoside compound comprising optionally repeating the step of reacting an alcohol compound of formula (2a) with a 2-phosphonoyl-1,2-transglycoside compound of formula (3a) at least once, formula 2(a) comprising:

Q 2a -OH  (2a)

wherein Q 2a is one of the groups given below,

A 1 is

R 2′ and R 3′ are combined with each other to form an alkylene having 2 or 4 carbon atoms, wherein the alkylene is optionally substituted with alkyl having 1 to 4 carbon atoms, or optionally comprises an intervening phenylene, m′ and n′ are each an integer of 0 or 1; R 7 , R 8 , R 9 are the same or different and are each a protective group for the saccharide hydroxyl group, and E 1 is methylene or carbonyl, Z 2 is a group —S—R 1′ , a group —SO—R 1′ , a group —Se—R 1′ , a group —O—C(═NH)CX′ 3 , a halogen atom, an alkoxyl, an alkenyloxy, a group —P(OR 1′ ) 3 or a group —PO(OR 1′ ) 3 ; R E is an alkyl comprising 1 to 20 carbon atoms, an aryl optionally substituted, or a heteroaromatic group, and X′ is a halogen atom; and

formula (3a) comprising:

Q 1a -O-Q 2a   (3a)

wherein Q 1a =

R 4 , R 5 and R 6 are the same or different and are each a protective group for the saccharide hydroxyl group, E is methylene or a carbonyl, and A is

wherein R 2 and R 3 are connected via an alkylene group having 2 to 4 carbon atoms, further wherein the alkylene group is optionally substituted with an alkyl group having 1 to 4 carbon atoms, or optionally comprises an intervening phenylene, and m and n are each an integer of 0 or 1;

and Q 2a is as defined above.

6. A process for preparing a 1,2-transglycoside compound of the formula (4) comprising reacting a base with a 2-phosphonoyl-1,2-transglycoside compound of formula (3), formula (3) comprising:

Q 1a -O-Q 2   (3)

wherein Q 1a =

R 4 , R 5 , R 6 and E are as defined below, and A is

wherein R 2 and R 3 are connected via an alkylene group having 2 to 4 carbon atoms, further wherein the alkylene group is optionally substituted with an alkyl group having 1 to 4 carbon atoms, or optionally comprises an intervening phenylene, and m and n are each an integer of 0 or 1;

wherein Q 2 is an alkyl having 1 to 4 carbon atoms, a cycloalkyl comprising 5 to 8 carbon atoms, optionally substituted, or one of the following groups

wherein L 1 is a group —OA 1 , —OG or —N(J 1 )(J 2 ), A 1 is a group shown below, G is a protective group for the saccharide hydroxyl, and J 1 and J 2 are each a hydrogen atom or a protective group for amino

R 2′ and R 3′ are combined with each other to form an alkylene having 2 or 4 carbon atoms, further, wherein the alkylene is optionally substituted with alkyl having 1 to 4 carbon atoms, or optionally comprises an intervening phenylene, m′ and n′ are each an integer of 0 or 1, Z 1 , X′, R 7 , R 8 , R 9 , and E 1 are as defined below;

formula (4) comprising:

Q 3 -O-Q 4   (4)

wherein Q 3 =

R 4 , R 5 , R 6 are the same or different and are each a protective group for the saccharide hydroxyl group, and E is methylene or a carbonyl, and

Q 4 is an alkyl comprising 1 to 4 carbon atoms, a cycloalkyl comprising 5 to 8 carbon atoms, optionally substituted, or one of the groups given below

wherein L 2 is the group —OH, —OG or —N(J 1 )(J 2 ), Z 1 is a group —S—R 1′ , a group —SO—R 1′ , a group —Se—R 1′ , a group —O—C(═NH)CX' 3 , a halogen atom, an alkoxyl, an alkenyloxy, a group —P(OR 1′ ) 3 , a group —PO(OR 1′ ) 3 or —OG 1 , R 1′ is an alkyl comprising 1 to 20 carbon atoms, an aryl optionally substituted, or a heteroaromatic group, X′ is a halogen atom, G 1 is a protective group for the saccharide hydroxyl, R 7 , R 8 and R 9 are the same or different and are each a protective group for the saccharide hydroxyl group, E 1 is methylene or a carbonyl, G is a protective group for the saccharide hydroxyl, and J 1 and J 2 are each a hydrogen atom or a protective group for amino.