Process for Producing 1,2-Trans-Glycoside Compound
AssigneeOtsuka Chemical Co., Ltd.
InventorShigeru Yamago
Life of this patent
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Abstract
In preparing a glycoside compound from (a) a furanose compound or pyranose compound, and (b) an alcohol compound, a process for preparing a glycoside compound in which glycosidic bond locates selectively trans form relative to C-2 hydroxyl group, the process comprising using a furanose compound wherein the hydroxyl at the 2-position may have a substituent protected with a group A, or a pyranose compound which may have a substituent wherein R2 and R3 are the same or different and are each alkyl having 1 to 4 carbon atoms or aryl having or not having a substituent, or R2 and R3 are combined to form alkylene having 2 to 4 carbon atoms (the alkylene may be substituted with alkyl having 1 to 4 carbon atoms, or may have intervening phenylene), and m and n are each an integer of 0 or 1.
Claims9
In preparing a glycoside compound from (a) a furanose compound or pyranose compound, and (b) an alcohol compound, a process for preparing a glycoside compound in which glycosidic bond locates selectively trans form relative to C-2 hydroxyl group, the process comprising using a furanose compound wherein the hydroxyl at the 2-position may have a substituent protected with a group A, or a pyranose compound which may have a substituent
- wherein R2 and R3 are the same or different and are each alkyl having 1 to 4 carbon atoms or aryl having or not having a substituent, or R2 and R3 are combined to form alkylene having 2 to 4 carbon atoms (the alkylene may be substituted with alkyl having 1 to 4 carbon atoms, or may have intervening phenylene), and m and n are each an integer of 0 or 1.
A process for preparing a 2-phosphonoyl-1,2-transglycoside compound of the formula (3) comprising reacting an alcohol compound of the formula (2) with a 2-phosphonoylpyranose compound of the formula (1)
- wherein Z is a group —S—R1, group —SO—R1, group —Se—R1, group —O—C(═NH)CX3, halogen atom, alkoxyl, alkenyloxy, group —P(OR1)3 or group —PO(OR1)3, R1 being alkyl having 1 to 20 carbon atoms, aryl having or not having a substituent or heteroaromatic group, X being a halogen atom, R4, R5 and R6 may be the same or different and are each a protective group for the saccharide hydroxyl group, E is methylene or carbonyl, and A is as defined above
- Q2-OH (2)
- wherein Q2 is alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 8 carbon atoms and having or not having a substituent at an optional position or one of the following groups
- wherein L1 is a group —OA1, —OG or —N(J1) (J2), A1 being a group shown below, G being a protective group for the saccharide hydroxyl, and J1 and J2 being each a hydrogen atom or a protective group for amino
- R2′ and R3′ are the same or different and are each alkyl having 1 to 4 carbon atoms or aryl having or not having a substituent, or R2′ and R3′ are combined with each other to form alkylene having 2 to 4 carbon atoms (the alkylene may be substituted with alkyl having 1 to 4 carbon atoms or may have an intervening phenylene), m′ and n′ are each an integer of 0 or 1. Z1 is a group —S—R1′, group —SO—R1′, group —Se—R1′, group —O—C(═NH)CX′3, halogen atom, alkoxyl, alkenyloxy, group —P(OR1′)3, group —PO(OR1′)3 or —OG1, R1′ being alkyl having 1 to 20 carbon atoms, aryl having or not having a substituent or heteroaromatic group, X′ being a halogen atom, G1 being a protective group for the saccharide hydroxyl, R7, R8 and R9 may be the same or different and are each a protective group for the saccharide hydroxyl group, E1 is methylene or carbonyl
- wherein Q2, A, R4, R5 and R6 are as defined above.
A process for preparing a 2-phosphonoyl-1,2-transglycoside compound of the formula (3a) comprising reacting an alcohol compound of the formula (2a) with a 2-phosphonoylpyranose compound of the formula (1)
- Q2a-OH (2a)
- wherein Q2a is one of the groups given below, A1, R7, R8, R9 and E1 are as defined above, Z2 is a group —S—R1′, group —SO—R1′, group —Se—R1′, group —O—C(═NH)CX′3, halogen atom, alkoxyl, alkenyloxy, group —P(OR1′)3 or group —PO(OR1′)3, and R1′ and X′ are as defined above
- wherein Q1a and Q2a are as defined above.
A process for preparing a 2-phosphonoyl-1,2-transglycoside compound comprising repeating the step of reacting an alcohol compound with a 2-phosphonoyl-1,2-transglycoside compound of the formula (3a) at least once.
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 the formula (3)
- wherein R4, R5, R6 and E are as defined above, and Q4 is alkyl having 1 to 4 carbon atoms, cycloalkyl having 5 to 8 carbon atoms and having or not having a substituent at an optional position or one of the groups given below
- wherein L2 is the group —OH, —OG or —N(J1) (J2), and Z1, R7, R8, R9, E1, G, J1 and J2 are as defined above.
A phosphonoylpyranose compound of the formula (1).
A 2-phosphonoyl-1,2-transglycoside compound of the formula (3).
A 2-phosphonoyl-1,2-transglycoside compound of the formula (3a).
Dependencies are inferred from the claim text.