Sialic acid derivatives and process therefor
First Claim
1. A process for producing ganglioside GD3 having the general formulae (8) and (9):
- ##STR15## (a) deacetylating a compound (3) having the following formula (3);
##STR16## , to produce a compound (4) having the following formula (4);
##STR17## (b) tritylating said compound (4), to produce a compound (5) having the following formula (5);
##STR18## wherein Tr is a trityl group, (c) acetylating said compound (5), to produce a compound (6) having the following formula (6);
##STR19## wherein Tr is defined above, (d) detritylating said compound (6), to produce a compound (7) having the following formula (7);
##STR20## , and then (e) reacting said compound (7) with a compound (2) having the following formula (2);
##STR21##
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Abstract
The present invention relates to sialic acid derivatives. According to the present invention, there is provided sialic acid derivatives having the general formula (I): ##STR1## wherein, R1 represents hydrogen, an acetyl group, a trityl group, ##STR2## (R5 represents hydrogen or an acetyl group and R6 represents hydrogen, sodium or a methyl group).
R2 represents hydrogen or an acetyl group,
one of R3 and R4 represents ##STR3## (R7 represents a hydrogen atom or an acetyl group, R8 represents a hydrogen atom, an acetyl group or a benzyl group, R9 represents a hydrogen atom, an acetyl group, a benzyl group or ##STR4## wherein R10 represents a hydrogen atom or a benzoyl group), while the other represents --COOR11 wherein R11 represents hydrogen, sodium, or a methyl group.
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Citations
11 Claims
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1. A process for producing ganglioside GD3 having the general formulae (8) and (9):
- ##STR15## (a) deacetylating a compound (3) having the following formula (3);
##STR16## , to produce a compound (4) having the following formula (4);
##STR17## (b) tritylating said compound (4), to produce a compound (5) having the following formula (5);
##STR18## wherein Tr is a trityl group, (c) acetylating said compound (5), to produce a compound (6) having the following formula (6);
##STR19## wherein Tr is defined above, (d) detritylating said compound (6), to produce a compound (7) having the following formula (7);
##STR20## , and then (e) reacting said compound (7) with a compound (2) having the following formula (2);
##STR21##
- ##STR15## (a) deacetylating a compound (3) having the following formula (3);
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2. A process for producing a compound (7) having the following formula (7):
- ##STR22## wherein ##STR23## is an OAc group and ##STR24## is an OBn group (Bn is a benzyl group), comprising;
(a) deallylating a compound (1) having the following formula (1);
##STR25## wherein ##STR26## is defined above, to produce a compound (2) having the following formula (2);
##STR27## wherein ##STR28## is defined above, (b) chlorinating said compound (2) to produce a compound (3) having the following formula (3);
##STR29## wherein ##STR30## is defined above, (c) reacting said compound (3) with benzyl lactose, to produce compounds (4) and (5) having the following formulae (4) and (5);
##STR31## wherein ##STR32## and ##STR33## are defined above, and then (d) acetylating said compound (5).
- ##STR22## wherein ##STR23## is an OAc group and ##STR24## is an OBn group (Bn is a benzyl group), comprising;
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3. A process for producing a compound having the following formula (13):
- ##STR34## comprising;
(a) acetylating a compound (4) having the following formula (4);
##STR35## wherein ##STR36## is an OAc group and ##STR37## is an OBn group (Bn is a benzyl group), to produce a compound (6) having the following formula (6);
##STR38## wherein ##STR39## and ##STR40## are defined above, and then (b) debenzylating said compound (6), to produce a compound (8) having the following formula (8);
##STR41## wherein ##STR42## is defined above. (c) acetylating said compound (8), to produce a compound (9) having the following formula (9);
##STR43## wherein ##STR44## is defined above, (d) selectively deacetylating said compound (9), to produce a compound (10) having the following formula (10);
##STR45## wherein ##STR46## is defined above, (e) reacting said compound (10) with trichloroacetonitrile to produce a compound (11) having the following formula (11);
##STR47## wherein ##STR48## is defined above, (f) reacting said compound (11) with benzoylceramide, to produce a compound (12) having the following formula (12);
##STR49## wherein ##STR50## is defined above and Bz is a benzoyl group, and then (g) hydrolyzing said compound (12).
- ##STR34## comprising;
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4. A process for producing a compound (7) having the following formula (7):
- ##STR51## wherein ##STR52## is an OAc group and ##STR53## is an OBn group (Bn is a benzyl group), comprising acetylating a compound (6) having the following formula (6);
##STR54## wherein ##STR55## and ##STR56## are defined above. - View Dependent Claims (5, 6)
- ##STR51## wherein ##STR52## is an OAc group and ##STR53## is an OBn group (Bn is a benzyl group), comprising acetylating a compound (6) having the following formula (6);
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7. A process for producing a compound (14) having the following formula (14):
- ##STR61## comprising;
(a) acetylating a compound (5) having the following formula (5);
##STR62## wherein ##STR63## is an OAc group and ##STR64## is an OBn group (Bn is a benzyl group), to produce a compound (8) having the following formula (8);
##STR65## wherein ##STR66## and ##STR67## are defined above, (b) debenzylating said compound (8), to produce a compound (9) having the following formula (9);
##STR68## wherein ##STR69## is defined above, (c) acetylating said compound (9), to produce a compound (10) having the following formula (10);
##STR70## wherein ##STR71## is defined above, (d) deacetylating said compound (10), to produce a compound (11) having the following formula (11);
##STR72## wherein ##STR73## is defined above, (e) reacting said compound (11) with Cl3 CCN, to produce a compound (12) having the following formula (12);
##STR74## wherein ##STR75## is defined above, (f) reacting said compound (12) with benzoylceramide, to produce a compound (13) having the following formula (13);
##STR76## wherein ##STR77## is defined above, and then (g) deactylating, debenzylating and then saponifying said compound (13). - View Dependent Claims (8, 9)
- ##STR61## comprising;
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10. A sialic acid derivative having the formula (I):
- ##STR82## wherein R1 represents ##STR83## (R5 represents hydrogen or an acetyl group and R6 represents hydrogen, sodium or a methyl group)
R2 represents hydrogen or an acetyl group, one of R3 and R4 represents --OCH2 CHCH2, or ##STR84## while the other represents -COOR11, wherein R11 represents hydrogen, sodium or a methyl group.
- ##STR82## wherein R1 represents ##STR83## (R5 represents hydrogen or an acetyl group and R6 represents hydrogen, sodium or a methyl group)
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11. A sialic acid derivative having the formula (I):
- ##STR85## wherein R1 represents hydrogen, an acetyl group, a trityl group, ##STR86## (R5 represents hydrogen or an acetyl group and R6 represents hydrogen, sodium or a methyl group)
R2 represents hydrogen or an acetyl group, one of R3 and R4 represents ##STR87## (R7 represents hydrogen or an acetyl group, R8 represents hydrogen, an acetyl group or a benzyl group, R9 represents hydrogen, an acetyl group, a benzyl group or ##STR88## wherein R10 represents hydrogen or a benzoyl group), while the other represents -COOR11 wherein R11 represents hydrogen, sodium, or a methyl group.
- ##STR85## wherein R1 represents hydrogen, an acetyl group, a trityl group, ##STR86## (R5 represents hydrogen or an acetyl group and R6 represents hydrogen, sodium or a methyl group)
Specification