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US4618675A
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Derivatives and reduction products of D-glucopyranosyl-alpha(1→5)-d-arabinonic acid; and production of same
Assignee: Sueddeutsche Zucker AG
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Filing: 1983-12-16
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Granted: 1986-10-21
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Expires: 2003-12-16
Abstract
Abstract The invention relates to derivatives and reduction products of D-glucopyranosyl-alpha(1→5)-d-arabinonic acid, having the general formula: ##STR1## wherein X is one of the following groups: --COOM, --COOR', CONH 2 or --CH 2 OH, where M is an alkali metal and R' is an alkyl group; and where R is a hydrogen atom or an acyl group. The compounds of formula (I) include compounds in which the arabinonic acid chain is closed in a lactone ring. A method for producing the derivatives and reaction products is described, and uses therefor are also provided.
Inventors
- 👤 Frieder W. Lichtenthaler
- 👤 Roger G. Klimesch
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 01:20
CPC Classifications
C; C07; C07H; C07H15/00; C07H15/02; C07H15/04; A; A23; A23L; A23L27/00; A23L27/30; A23L27/33; C07H15/26
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
94 words
Derivatives of D-glucopyranosyl-alpha-(1→5)-D-arabinonic acid of the formula: ##STR5## wherein X is a member selected from the group consisting of --COOM, --COOR', --CONH 2 , and --CH 2 OH, and M is an alkali metal and R' is an alkyl group having 1 to 20 carbon atoms; and wherein R is a hydrogen atom or an acyl group having 1 to 20 carbon atoms; the compounds of formula (I) including those aliphatic acid group is closed in a lactone ring represented by the formula: ##STR6## wherein R has the same meaning as set forth above.
Claim 2
Dependent Claim
94 words
Derivatives of D-glucopyranosyl-alpha-(1→5)-D-arabinonic acid of the formula: ##STR5## wherein X is a member selected from the group consisting of --COOM, --COOR', --CONH 2 , and --CH 2 OH, and M is an alkali metal and R' is an alkyl group having 1 to 20 carbon atoms; and wherein R is a hydrogen atom or an acyl group having 1 to 20 carbon atoms; the compounds of formula (I) including those aliphatic acid group is closed in a lactone ring represented by the formula: ##STR6## wherein R has the same meaning as set forth above.
Claim 3
Dependent Claim
25 words
A compound according to claim 1, wherein X is --CH 2 OH and R is H; the resulting compound being D-glucopyranosyl-alpha-(1→5))-D-arabinitol, of the formula: ##STR7##
Claim 4
Dependent Claim
26 words
A compound according to claim 1, wherein X is --COOK and R is H; the resulting compound being D-glucopyranosyl-alpha--(1→5)-D-arabinonic acid potassium salt of the formula: ##STR8##
Claim 5
Dependent Claim
27 words
A compound according to claim 1, wherein X is --COOCH 3 and R is H; the resulting compound being D-glucopyranosyl-alpha-(1→5)-D-arabinonic acid methyl ester of the formula: ##STR9##
Claim 6
Dependent Claim
30 words
A compound according to claim 1, wherein X is --COOCH 3 , and R is --COCH 3 ; the resulting compound being 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl-alpha(1→5)-2,3,4-tri-O-acetyl-D-arabinonic acid methyl ester of the formula: ##STR10##
Claim 7
Dependent Claim
27 words
A compound according to claim 1, wherein X is --CONH 2 and R is H; the resulting compound being D-glucopyranosyl-alpha (1→5)-D-arabinonic acid amide of the formula: ##STR11##
Claim 8
Dependent Claim
31 words
A compound according to claim 1, wherein the arabinonic acid is closed in a lactone ring and R is H; the resulting compound being D-glucopyranosyl-alpha(1→5)-D-arabinonic acid gamma-lactone, of the formula: ##STR12##
Claim 9
Dependent Claim
35 words
A compound according to claim 1, wherein the arabinonic ring is closed in a lactone ring and R is --COC 6 H 5 ; the resulting compound being 5-O-(2,3,4,6-tetra-O-benzoyl-alpha-D-glucopyranosyl)-2,3-di-O-benzoyl-D-arabinonic acid gamma-lactone of the formula: ##STR13##
Claim 10
Dependent Claim
37 words
A compound according to claim 1, wherein X is --CH 2 OCOC 6 H 5 and R is --COC 6 H 5 , the resulting compound being the octabenzoate of D-glucopyranosyl-alpha(1→5)-D-arabinonic acid alcohol of the formula: ##STR14##
Claim 11
Dependent Claim
135 words
A process of preparing derivatives of D-glucopyranosyl-alpha(1→5)-D-arabinonic acid of the formula: ##STR15## which comprises: oxidizing isomaltulose in an alkali metal hydroxide with an oxygen containing gas, and isolating the resulting salts from the reaction mixture by direct crystallization thereby providing the alkali metal salt of D-glucopyranosyl-alpha(1→5)-D-arabinonic acid wherein X is a member selected from the group consisting of --COOM, --COOR', --CONH 2 , and --CH 2 , and M is an alkali metal and R' is an alkyl group having 1 to 20 carbon atoms; and wherein R is a hydrogen atom or an acyl group having 1 to 20 carbon atoms, the compounds of formula (I) including those in which the aliphatic group is closed in a lactone ring represented by the formula: ##STR16## where R has the same meaning as set forth above.
Claim 12
Dependent Claim
135 words
A process of preparing derivatives of D-glucopyranosyl-alpha(1→5)-D-arabinonic acid of the formula: ##STR15## which comprises: oxidizing isomaltulose in an alkali metal hydroxide with an oxygen containing gas, and isolating the resulting salts from the reaction mixture by direct crystallization thereby providing the alkali metal salt of D-glucopyranosyl-alpha(1→5)-D-arabinonic acid wherein X is a member selected from the group consisting of --COOM, --COOR', --CONH 2 , and --CH 2 , and M is an alkali metal and R' is an alkyl group having 1 to 20 carbon atoms; and wherein R is a hydrogen atom or an acyl group having 1 to 20 carbon atoms, the compounds of formula (I) including those in which the aliphatic group is closed in a lactone ring represented by the formula: ##STR16## where R has the same meaning as set forth above.
Claim 13
Dependent Claim
36 words
The process of claim 10, wherein the alkali metal salt of the D-glucopyranosyl-alpha(1→5)-D-arabinonic acid is treated with an alkanol in the presence of an ion exchange medium, thereby providing the corresponding alkyl ester of D-glucopyranosyl-alpha(1→5)-D-arabinonic aicd.
Claim 14
Dependent Claim
33 words
The process of claim 10, wherein the alkali metal salt of D-glucopyranosyl-alpha(1→5)-D-arabinonic acid is treated with an acidic ion exchange medium is an aqueous solution, thereby providing the corresponding gamma-lactone of D-glucopyranosyl-alpha(1→5)-D-arabinonic acid.
Claim 15
Dependent Claim
26 words
The process of claim 11, wherein the alkyl ester of D-glucopyranosyl-alpha(1→5)-D-arabinonic acid is treated with anhydrous ammonia in methanol, thereby providing the corresponding D-glucopyranosyl-alpha(1→5)-D-arabinonic acid amide.
Claim 16
Dependent Claim
48 words
The process of claim 11, wherein one of the D-glucopyranosyl-alpha(1→5)-D-arabinonic acid alkyl ester and a heptaacylate of the D-glucopyranosyl-alpha(1→5)-D-arabinonic alkyl ester is reduced with one of a complex metal hydride and catalytically activated hydrogen, and the resulting D-glucopyranosyl-alpha(1→5)-D-arabinitol is then isolated by crystallization, thereby providing the corresponding D-glucopyranosyl-alpha(1→5)-D-arabinitol.
Claim 17
Dependent Claim
38 words
The process of claim 11, wherein the D-glucopyranosyl-alpha(1→5)-D-arabinonic acid alkyl ester is D-glucopyranosyl-alpha(1→5)-D-arabinonic acid methyl ester; and the D-glycopyranosyl-alpha(1→5)-D-arabinonic acid is methyl ester acetylated with acetic anhydride in an anhydrous solvent, thereby providing hepta-O-acetyl D-glucopyranosyl-alpha(1→5)-D-arabinonic acid methyl ester.
Claim 18
Dependent Claim
48 words
The process of claim 12, wherein one of the D-glucopyranosyl-alpha(1→5)-D-arabinonic acid gamma-lactone and a hexabenzoate of said D-glucopyranosyl-alpha(1→5)-D-arabinonic acid gamma lactone is reduced with one of a complex metal hydride and catalytically activated hydrogen, and the resulting D-glucopyranosyl-alpha(1→5)-D-arabinitol is then isolated by crystallization, thereby providing the corresponding D-glucopyranosyl-alpha(1→5)-D-arabinitol.
Claim 19
Dependent Claim
26 words
The process of claim 12, wherein the gamma lactone of D-glucopyranosyl-alpha(1→5)-D-arabinonic acid is benzoylated with benzoyl chloride in an anhydrous solvent, thereby providing hexa-O-benzoyl D-glucopyranosyl-alpha(1→5)-D-arabinonic gamma-lactone.
Claim 20
Dependent Claim
23 words
The process of claim 14, wherein the D-glucopyranosyl-alpha(1→5)-D-arabinitol is benzoylated with benzoyl chloride in an anhydrous solvent, thereby providing the octabenzoate of D-glucopyranosyl-alpha(1→5)-D-arabinitol.
Claim 21
Dependent Claim
19 words
The process of claim 16 wherein the D-glucopyranosyl-alpha(1→5)-D-arabinitol is benzoylated with benzoyl chloride, thereby providing the octabenzoate of D-glucopyranosyl-alpha(1→5)-D-arabinitol.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1989-10-20 | 1990-04-21 | 1990-10-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-10-20 | 1994-04-21 | 1994-10-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-10-20 | 1998-04-21 | 1998-10-21 | $7700.00 | Window Closed / Lapsed |