US4659810A
Expired / Lapsed
US
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Process for the preparation of 1-azidoaldoses
Assignee: Hoechst AG
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Filing: 1985-06-28
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Granted: 1987-04-21
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Expires: 2005-06-28
Abstract
Abstract 1-Azidoaldoses are obtained by reacting 1-fluoroaldoses with metal azides in polar, water-miscible, preferably water-containing, solvents. The hydroxyl groups do not react at the same time, so that they need not be protected or can be present in a derivatized form.
Inventors
- 👤 Joachim Thiem
- 👤 Hans-Matthias Deger
- 👤 Cenek Kolar
- 👤 Matthias Kreuzer
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-06 08:49
CPC Classifications
C; C07; C07H; C07H15/00; C07H15/02; C07H15/04
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
24 words
The process for the manufacture of 1-azidoaldoses which comprises reacting a 1-fluoro-aldose with a metal azide in the presence of a polar, water-miscible solvent.
Claim 2
Dependent Claim
24 words
The process for the manufacture of 1-azidoaldoses which comprises reacting a 1-fluoro-aldose with a metal azide in the presence of a polar, water-miscible solvent.
Claim 3
Dependent Claim
30 words
A process as claimed in claim 1, wherein the reaction is carried out at a temperature in the range from 0° C. to the boiling point of the reaction system.
Claim 4
Dependent Claim
24 words
A process as claimed in claim 2, wherein the reaction is carried out at a temperature in the range from 40° to 120° C.
Claim 5
Dependent Claim
24 words
A process as claimed in claim 3, wherein the reaction is carried out at a temperature in the range from 60° to 100° C.
Claim 6
Dependent Claim
15 words
A process as claimed in claim 3, wherein the metal azide is an alkali azide.
Claim 7
Dependent Claim
35 words
A process as claimed in claim 1, wherein the reaction is carried out at a temperature in the range from 0° C. to 60° C. and the metal azide is an alkaline earth metal azide.
Claim 8
Dependent Claim
22 words
A process as claimed in claim 1, wherein the polar water-miscible solvent is a lower alkanol, acetonitrile, an amide or an ether.
Claim 9
Dependent Claim
14 words
A process as claimed in claim 1, wherein the reaction mixture also contains water.
Claim 10
Dependent Claim
23 words
A process as claimed in claim 1, wherein the salts generated are removed from the reaction mixture by means of an ion exchanger.
Claim 11
Dependent Claim
36 words
A process as claimed in claim 1, wherein the salts generated are removed from the reaction mixture by means of a molecular sieve in water or a mixture thereof with at least one water-miscible organic solvent.
Claim 12
Dependent Claim
22 words
A process as claimed in claim 1, wherein the metal azide is an alkaline earth metal azide or an alkali metal azide.
Claim 13
Dependent Claim
19 words
A process as claimed in claim 11, wherein the metal azide is sodium azide, potassium azide or calcium azide.
Claim 14
Dependent Claim
32 words
A process as claimed in claim 12, wherein the metal azide is calcium azide and the reaction is carried out at a temperature in the range from ambient temperature to 60° C.
Claim 15
Dependent Claim
18 words
A process as claimed in claim 1, wherein the alkaline earth metal azide is reacted in statu nascendi.
Claim 16
Dependent Claim
29 words
A process as claimed in claim 1, wherein the metal azide is applied at least in the stoechiometric amount and at most in triple amount of the stoechiometric amount.
Claim 17
Dependent Claim
12 words
A process as claimed in claim 1, wherein the 1-fluoro-aldose is unprotected.
Claim 18
Dependent Claim
22 words
A process as claimed in claim 1, wherein the 1-azidoaldoses are prepared directly and without the use of intermediates carrying protective groups.
References Cited (Backward Citations)
US4220643A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1990-04-20 | 1990-10-20 | 1991-04-21 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-04-20 | 1994-10-20 | 1995-04-21 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-04-20 | 1998-10-20 | 1999-04-21 | $7700.00 | Window Closed / Lapsed |