US4495346A
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Method of preparing a disaccharide
Assignee: Wisconsin Alumni Research Foundation
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Filing: 1982-10-06
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Granted: 1985-01-22
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Expires: 2002-10-06
Abstract
Abstract Novel disaccharides useful in preparing analogs of lipid A are prepared by first preparing novel precursors of the reducing and non-reducing moieties of the lipid A molecule and then catalytically coupling the precursors.
Inventors
- 👤 Laurens Anderson
- 👤 Mina A. Nashed
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 16:11
CPC Classifications
C; C07; C07H; C07H5/00; C07H5/04; C07H5/06; C07H11/00; C07H11/04
Claims Analysis
Total Claims: 5
Claim 1
Independent Claim
103 words
A method of preparing a disaccharide of the formula: ##STR10## in which R is an alkyl, hydroxyalkyl or protected hydroxyalkyl group of 7 to 19 carbon atoms; R 1 is selected from allyl, benzyl, 1-propenyl, or trichloroethyl; R 3 ' is selected from allyl, crotyl, 2-methoxyethoxymethyl, methylthiomethyl, or benzyl; R 4 ' is hydrogen, chloroacetyl, or β-benzoylpropionyl; and R 4 is hydrogen or ##STR11## said method comprising reacting a compound of the formula: ##STR12## with a compound of the formula: ##STR13## in which all symbols are as previously defined, in the presence of a coupling catalyst selected from p-toluenesulfonic acid and 2,6-dimethylpyridinium p-toluenesulfonate.
Claim 2
Independent Claim
103 words
A method of preparing a disaccharide of the formula: ##STR10## in which R is an alkyl, hydroxyalkyl or protected hydroxyalkyl group of 7 to 19 carbon atoms; R 1 is selected from allyl, benzyl, 1-propenyl, or trichloroethyl; R 3 ' is selected from allyl, crotyl, 2-methoxyethoxymethyl, methylthiomethyl, or benzyl; R 4 ' is hydrogen, chloroacetyl, or β-benzoylpropionyl; and R 4 is hydrogen or ##STR11## said method comprising reacting a compound of the formula: ##STR12## with a compound of the formula: ##STR13## in which all symbols are as previously defined, in the presence of a coupling catalyst selected from p-toluenesulfonic acid and 2,6-dimethylpyridinium p-toluenesulfonate.
Claim 3
Dependent Claim
15 words
The method of claim 1 in which R is an alkyl of 15 carbon atoms.
Claim 4
Dependent Claim
12 words
The method of claim 1 in which R 3 ' is benzyl.
Claim 5
Dependent Claim
11 words
The method of claim 1 in which R 4 is hydrogen.
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) | 1988-01-22 | 1988-07-23 | 1989-01-22 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-01-22 | 1992-07-23 | 1993-01-22 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-01-22 | 1996-07-23 | 1997-01-22 | $7700.00 | Window Closed / Lapsed |