Patent US2565548A successfully refreshed from Google Patents.
Patent US4751291A successfully refreshed from Google Patents.
US4751291A
Expired / Lapsed
US
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Process for the preparation of glycosyl fluorides protected on the oxygen
Assignee: Hoechst AG
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Filing: 1986-09-12
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Granted: 1988-06-14
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Expires: 2006-09-12
Abstract
Abstract Glycosyl halides which are O-acylated or O-alkylated at least in the 2-position are transhalogenated with alkali metal hydrogen difluorides in a polar-aprotic solvent and, if appropriate, the product is anomerized with the addition of less than the stoichiometric amounts of an inorganic fluoride with a Lewis acid character. Depending on the substrate, the glycosyl fluorides with the 1,2-trans or 1,2-cis configuration are obtained.
Inventors
- 👤 Joachim Thiem
- 👤 Hans-Matthias Deger
- 👤 Wolfram Fritsche-Lang
- 👤 Matthias Kreuzer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 16:54
CPC Classifications
C; C07; C07H; C07H5/00; C07H5/02; C07H13/00; C07H13/02; C07H13/04; C07H15/00; C07H15/18
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
64 words
A process for the preparation of a 1,2-trans- or -cis-glycosyl fluoride which is O-acylated or O-alkylated at least in the 2-position, by transhalogenation, which comprises reacting the corresponding O-acylated or O-alkylated glycosyl halide with an alkali metal hydrogen difluoride in a polar-aprotic solvent and anomerizing the product by addition of less than the stoichiometric amount of an inorganic fluoride with a Lewis acid character.
Claim 2
Dependent Claim
64 words
A process for the preparation of a 1,2-trans- or -cis-glycosyl fluoride which is O-acylated or O-alkylated at least in the 2-position, by transhalogenation, which comprises reacting the corresponding O-acylated or O-alkylated glycosyl halide with an alkali metal hydrogen difluoride in a polar-aprotic solvent and anomerizing the product by addition of less than the stoichiometric amount of an inorganic fluoride with a Lewis acid character.
Claim 3
Dependent Claim
18 words
The process as claimed in claim 1, wherein a chloride or bromide is employed as the glycosyl halide.
Claim 4
Dependent Claim
21 words
The process as claimed in claim 1, wherein a glycosyl halide in which all the hydroxyl groups are protected is employed.
Claim 5
Dependent Claim
19 words
The process as claimed in claim 1, wherein potassium hydrogen difluoride is employed as the alkali metal hydrogen difluoride.
Claim 6
Dependent Claim
26 words
The process as claimed in claim 1, wherein the inorganic fluoride with a Lewis acid character is used in less than 25% of the stoichiometric amount.
Claim 7
Dependent Claim
24 words
The process as claimed in claim 1, which is carried out at a temperature in the range of from 10° C. to 100° C.
Claim 8
Dependent Claim
24 words
The process as claimed in claim 1, which is carried out at a temperature in the range of from 40° C. to 80° C.
Claim 9
Dependent Claim
68 words
A process for the preparation of a 1,2-trans- or -cis-glycosyl fluoride which is O-acylated dor O-alkylated at least in the 2-position, by transhalogenation, which comprises reacting the corresponding O-acylated or O-alkylated glycosyl halide with an alkali metal hydrogen difluoride in a polar-aprotic solvent and anomerizing the product by addition of less than the stoichiometric amount of BF 3 , SnF 4 , ZrF 4 or TiF 4 .
Claim 10
Dependent Claim
68 words
A process for the preparation of a 1,2-trans- or -cis-glycosyl fluoride which is O-acylated dor O-alkylated at least in the 2-position, by transhalogenation, which comprises reacting the corresponding O-acylated or O-alkylated glycosyl halide with an alkali metal hydrogen difluoride in a polar-aprotic solvent and anomerizing the product by addition of less than the stoichiometric amount of BF 3 , SnF 4 , ZrF 4 or TiF 4 .
Claim 11
Dependent Claim
21 words
The process as claimed in claim 8, wherein TiF 4 is employed as an inorganic fluoride with a Lewis acid character.
Claim 12
Dependent Claim
24 words
The process as claimed in claim 8, which is carried out at a temperature in the range of from 10° C. to 100° C.
Claim 13
Dependent Claim
24 words
The process as claimed in claim 8, which is carried out at a temperature in the range of from 40° C. to 80° C.
Claim 14
Dependent Claim
43 words
A process for the preparation of a 1,2-trans- or -cis-glycosyl fluoride which is O-acylated or O-alkylated at least in the 2-position, by transhalogenation, which comprises reacting the corresponding O-acylated or O-alkylated glycosyl halide with an alkali metal hydrogen difluoride in a polaraprotic solvent.
Claim 15
Dependent Claim
43 words
A process for the preparation of a 1,2-trans- or -cis-glycosyl fluoride which is O-acylated or O-alkylated at least in the 2-position, by transhalogenation, which comprises reacting the corresponding O-acylated or O-alkylated glycosyl halide with an alkali metal hydrogen difluoride in a polaraprotic solvent.
Claim 16
Dependent Claim
18 words
The process as claimed in claim 12, wherein a chloride or bromide is employed as the glycosyl halide.
Claim 17
Dependent Claim
21 words
The process as claimed in claim 12, wherein a glycosyl halide in which all the hydroxyl groups are protected is employed.
Claim 18
Dependent Claim
19 words
The process as claimed in claim 12, wherein potassium hydrogen difluoride is employed as the alkali metal hydrogen difluoride.
Claim 19
Dependent Claim
24 words
The process as claimed in claim 12, which is carried out at a temperature in the range of from 10° C. to 100° C.
Claim 20
Dependent Claim
24 words
The process as claimed in claim 12, which is carried out at a temperature in the range of from 40° C. to 80° C.
References Cited (Backward Citations)
US4659810A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1991-06-14 | 1991-12-14 | 1992-06-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-06-14 | 1995-12-14 | 1996-06-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-06-14 | 1999-12-14 | 2000-06-14 | $7700.00 | Window Closed / Lapsed |