US4202829A
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Process for preparing 1α-hydroxylated compounds
Assignee: Wisconsin Alumni Research Foundation
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Filing: 1978-12-13
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Granted: 1980-05-13
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Expires: 1998-12-13
Abstract
Abstract A method for directly introducing an oxygen function at carbon 1 of the vitamin D molecule or precursors of derivatives thereof which comprises subjecting such molecules to allylic oxidation utilizing selenium dioxide as the oxidizing agent.
Inventors
- 👤 Hector F. DeLuca
- 👤 Heinrich K. Schnoes
- 👤 David E. Hamer
- 👤 Herbert E. Paaren
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-26 14:11
CPC Classifications
C; C07; C07C; C07C401/00; C07C2601/00; C07C2601/12; C07C2601/14; C07C2601/16; C07C2602/00; C07C2602/02; C07C2602/14; C07C2602/24
Claims Analysis
Total Claims: 12
Claim 1
Independent Claim
105 words
A method for preparing 1α-hydroxylated compounds having the general formulae ##STR8## where R is selected from the group consisting of a substituted or unsubstituted cholesterol or ergosterol side chain group, and X is selected from the group consisting of hydrogen, hydroxy, acyl, O-lower alkyl, O-lower acyl, and O-aromatic acyl, which comprises subjecting compounds having the formulae ##STR9## to allylic oxidation, with the proviso that the 1-hydroxylated product of a compound of formula (2) be subsequently subjected to isomerization by irradiation with ultraviolet light and the 1-hydroxylated product of a compound of formula (3) be subsequently subjected to thermal isomerization and recovering the desired 1-hydroxylated product.
Claim 2
Independent Claim
105 words
A method for preparing 1α-hydroxylated compounds having the general formulae ##STR8## where R is selected from the group consisting of a substituted or unsubstituted cholesterol or ergosterol side chain group, and X is selected from the group consisting of hydrogen, hydroxy, acyl, O-lower alkyl, O-lower acyl, and O-aromatic acyl, which comprises subjecting compounds having the formulae ##STR9## to allylic oxidation, with the proviso that the 1-hydroxylated product of a compound of formula (2) be subsequently subjected to isomerization by irradiation with ultraviolet light and the 1-hydroxylated product of a compound of formula (3) be subsequently subjected to thermal isomerization and recovering the desired 1-hydroxylated product.
Claim 3
Dependent Claim
18 words
The method of claim 1 wherein the allylic oxidation is carried out with selenium dioxide as the oxidant.
Claim 4
Dependent Claim
25 words
The method of claim 1 wherein the allylic oxidation is carried out with selenium dioxide as the oxidant in the presence of an alkyl hydroperoxide.
Claim 5
Dependent Claim
41 words
The method of claim 1 wherein R has the formula ##STR10## wherein each of R 1 , R 2 and R 3 are selected from the group consisting of hydrogen, hydroxy, lower alkyl, O-lower alkyl, O-lower acyl, O-aromatic acyl, and fluorine.
Claim 6
Dependent Claim
18 words
The method of claim 4 wherein R 1 and R 3 are hydrogen and R 2 is hydroxy.
Claim 7
Dependent Claim
9 words
The method of claim 5 wherein X is hydroxy.
Claim 8
Dependent Claim
20 words
The method of claim 4 wherein R 1 , R 2 and R 3 are hydrogen and X is hydroxy.
Claim 9
Dependent Claim
50 words
The method of claim 1 wherein R has the formula ##STR11## wherein each of R 1 , R 2 and R 3 are selected from the group consisting of hydrogen, hydroxy, lower alkyl, O-lower alkyl, O-lower acyl, O-aromatic acyl, and fluorine, and wherein R 4 is hydrogen or lower alkyl.
Claim 10
Dependent Claim
22 words
The method of claim 8 wherein R 1 and R 3 are hydrogen, R 2 is hydroxy and R 4 is methyl.
Claim 11
Dependent Claim
9 words
The method of claim 9 wherein X is hydroxyl.
Claim 12
Dependent Claim
24 words
The method of claim 8 wherein R 1 , R 2 and R 3 are hydrogen, R 4 is methyl and X is hydroxyl.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-05-13 | 1983-11-12 | 1984-05-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-05-13 | 1987-11-12 | 1988-05-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-05-13 | 1991-11-12 | 1992-05-13 | $7700.00 | Window Closed / Lapsed |