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US4871837A
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Hydroxy protection groups
Assignee: Syn-Tek AB
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Filing: 1987-01-27
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Granted: 1989-10-03
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Expires: 2007-01-27
Abstract
Abstract The present invention concerns a method for preparing unprotected hydroxy compounds or acylated derivatives thereof by conversion of silyl alkyl-protected hydroxy compounds. The invention also relates to novel intermediates useful in the method and for other purposes.
Inventors
- 👤 Hans G. Magnusson
- 👤 Karl Jansson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 20:43
CPC Classifications
C; C07; C07H; C07H13/00; C07H13/02; C07H13/04; C07H13/06; C07F; C07F7/00; C07F7/02; C07F7/08; C07F7/0803; C07F7/081; C07F7/0812; C07H13/08; C07H15/00; C07H15/02; C07H15/04; C07H19/00; C07H19/02; C07H19/04; C07H19/044; C07H23/00; C07H3/00; C07H3/06
Claims Analysis
Total Claims: 32
Claim 1
Independent Claim
140 words
A method for preparing an unprotected hydroxy compound from a protected hydroxy compound of the general formula I ##STR15## in which R 1 is the non-hydroxy moiety of a hydroxy compound selected from the group consisting of hydroxy-containing amino acids, peptides containing at least one such acid, and carbohydrates or derivatives thereof; R 2 , R 3 , R 4 and R 5 which may be the same or different are hydrogen, C 1-4 alkyl or aryl; and R 6 , R 7 and R 8 which may be the same or different are C 1-4 alkyl phenyl, substituted phenyl or a carrier in which the compound of formula I is reacted with a Lewis acid followed by reaction with water forming a hydroxy compound of the general formula II R.sub.1 --OH in which R 1 is as defined above.
Claim 2
Independent Claim
140 words
A method for preparing an unprotected hydroxy compound from a protected hydroxy compound of the general formula I ##STR15## in which R 1 is the non-hydroxy moiety of a hydroxy compound selected from the group consisting of hydroxy-containing amino acids, peptides containing at least one such acid, and carbohydrates or derivatives thereof; R 2 , R 3 , R 4 and R 5 which may be the same or different are hydrogen, C 1-4 alkyl or aryl; and R 6 , R 7 and R 8 which may be the same or different are C 1-4 alkyl phenyl, substituted phenyl or a carrier in which the compound of formula I is reacted with a Lewis acid followed by reaction with water forming a hydroxy compound of the general formula II R.sub.1 --OH in which R 1 is as defined above.
Claim 3
Dependent Claim
22 words
A method according to claim 1 in which R 2 , R 3 , R 4 and R 5 each are hydrogen.
Claim 4
Dependent Claim
19 words
A method according to claim 1 in which R 6 , R 7 and R 8 each are methyl.
Claim 5
Dependent Claim
48 words
A method according to claim 1 in which the Lewis acid is BF 3 , ZnCl 2 , FeCl 3 , MgBr 2 , AlCl 3 , SnCl 4 , ZnBr 2 , TiCl 4 ., TiF 4 , BBr 3 , SnBr 4 or TiBr 4 .
Claim 6
Dependent Claim
38 words
A method according to claim 1 in which R 1 is the non-hydroxy moiety of a hydroxy-containing amino acid forming part of a peptide, and one of R 6 , R 7 and R 8 is a carrier.
Claim 7
Dependent Claim
31 words
The method of claim 1 in which the carrier is an organic or inorganic, polymeric or macromolecular structure which is attachable to the silicon atom of the compound of formula I.
Claim 8
Dependent Claim
32 words
The method of claim 1 in which R 1 is a carbohydrate moiety attached to the oxygen atom of Formula I through the 1-carbon atom of the carbohydrate, or a derivative thereof.
Claim 9
Dependent Claim
122 words
A method for preparing a compound of the general formula III R.sub.1 --O--A in which R 1 is the non-hydroxy moiety of hydroxy compound selected from the group consisting of hydroxy-containing amino acids, peptides containing at least one such acid, and carbohydrates or derivatives thereof; and A is an acyl group comprising reacting a protected hydroxy compound of the formula I ##STR16## in which R 1 is a defined above; and R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are as defined in claim 1, with a Lewis acid in the presence of an activated derivative of an acid of the general formula A--OH where S is as defined above.
Claim 10
Dependent Claim
22 words
A method according to claim 8 in which R 2 , R 3 , R 4 and R 5 each are hydrogen.
Claim 11
Dependent Claim
19 words
A method according to claim 8 in which R 6 , R 7 and R 8 each are methyl.
Claim 12
Dependent Claim
48 words
A method according to claim 8 in which the Lewis acid is BF 3 , ZnCl 2 , FeCl 3 , MgBr 2 , AlCl 3 , SnCl 4 , ZnBr 2 , TiCl 4 , TiF 4 , BBr 3 , SnBr 4 or TiBr 4 .
Claim 13
Dependent Claim
25 words
A method according to claim 8 in which the activated derivative of the acid of formula A--OH is an activated derivative of a carboxylic acid.
Claim 14
Dependent Claim
14 words
A method according to claim 12 in which the activated derivative is an anhydride.
Claim 15
Dependent Claim
18 words
A method according to claim 13 in which the anhydride is a symmetric anhydride or a mixed anhydride.
Claim 16
Dependent Claim
70 words
A method according to claim 13 in which the anhydride is selected from the group consisting of Valeric anhydride Dichlorofluoroacetic anhydride Butyric anhydride Isobutyric anhydride Isovaleric anhydride Trifluoroacetic anhydride Acetic anhydride Trimethylacetic anhydride Dichloroacetic anhydride Heptafluorobutyric anhydride N-butyric anhydride Nicotinic anhydride Hexanoic anhydride Heptanoic anhydride Chloroacetic anhydride Benzoic anhydride Propionic anhydride 3-Methylcrotonic acid anhydride Crotonic anhydride Trichloroacetic anhydride Oleic anhydride p-Nitrobenzoic anhydride p-Methoxybenzoic anhydride p-Trifluoroacetamidobenzoic anhydride p-Nitrobenzoic-acetic anhydride Stearic anhydride.
Claim 17
Dependent Claim
31 words
The method of claim 8 in which the carrier is an organic or inorganic, polymeric or macromolecular structure which is attachable to the silicon atom of the compound of formula I.
Claim 18
Dependent Claim
32 words
The method of claim 8 in which R 1 is a carbohydrate moiety attached to the oxygen atom of Formula I through the 1-carbon atom of the carbohydrate, or a derivative thereof.
Claim 19
Dependent Claim
52 words
A compound of the general formula IV: R.sub.1 --O--X in which R 1 is the non-hydroxy moiety of a hydroxy compound selected from the group consisting of hydroxy-containing amino acids, peptides containing at least one such amino acid and carbohydrates or derivatives thereof; and X is a residue of a Lewis acid.
Claim 20
Dependent Claim
52 words
A compound of the general formula IV: R.sub.1 --O--X in which R 1 is the non-hydroxy moiety of a hydroxy compound selected from the group consisting of hydroxy-containing amino acids, peptides containing at least one such amino acid and carbohydrates or derivatives thereof; and X is a residue of a Lewis acid.
Claim 21
Dependent Claim
47 words
A compound according to claim 18 in which X is selected from the group consisting of --BF 2 , --ZnCl, --ZnBr, --FeCl 2 , --MgBr, --AlCl 2 , and --SnCl 3 , --TiCl 3 , --TiF 3 , --BBr 2 , --SnBr 3 or --TiBr 3 .
Claim 22
Dependent Claim
32 words
The method of claim 18 in which R 1 is a carbohydrate moiety attached to the oxygen atom of Formula IV through the 1-carbon atom of the carbohydrate, or a derivative thereof.
Claim 23
Dependent Claim
77 words
A method for preparing a compound of formula R 1 --O--X, where X is a residue of a Lewis acid and R 1 is as defined in claim 1, comprising reacting a protected hydroxy compound of the formula I in which R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are as defined in claim 1 with a Lewis acid under dry conditions.
Claim 24
Dependent Claim
53 words
A compound of the general formula Ia ##STR17## wherein R 1 ' is a carbohydrate moiety containing two or more sugar units or a derivative thereof, and R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are as defined in claim 1.
Claim 25
Dependent Claim
61 words
A method for preparing a compound of the general formula Ia defined in claim 22 in which a compound of the general formula Ib ##STR18## wherein R 1 " is a partially protected carbohydrate moiety containing one or more sugar units less than the group R 1 ' is subjected to a glycosidation reaction followed by removal of the protective groups.
Claim 26
Dependent Claim
18 words
A method according to claim 23 in which the glycosidation is carried out by enzymatic or microbial means.
Claim 27
Dependent Claim
31 words
The method of claim 22 in which the carrier is an organic or inorganic, polymeric or macromolecular structure which is attachable to the silicon atom of the compound of formula I.
Claim 28
Dependent Claim
35 words
A carbohydrate derivative containing one or more sugar units and being acylated in the C-1 and C-2 positions of the reducing sugar unit, wherein the acyl groups in the C-1 and C-2 positions are different.
Claim 29
Dependent Claim
35 words
A carbohydrate derivative containing one or more sugar units and being acylated in the C-1 and C-2 positions of the reducing sugar unit, wherein the acyl groups in the C-1 and C-2 positions are different.
Claim 30
Independent Claim
95 words
A method for preparing a compound of the general formula V R.sub.10 --Y V in which R 10 is a carbohydrate moiety containing one or more sugar units and being attached to Y through the 1-carbon atom, and Y is an alcohol or thiol group in which a carbohydrate derivative containing one or more sugar units and acylated in the C-1 and C-2 positions of the reducing sugar unit, the acyl groups in the C-1 and C-2 positions being different, is reacted with a alcohol or a thiol in the presence of a Lewis acid.
Claim 31
Independent Claim
95 words
A method for preparing a compound of the general formula V R.sub.10 --Y V in which R 10 is a carbohydrate moiety containing one or more sugar units and being attached to Y through the 1-carbon atom, and Y is an alcohol or thiol group in which a carbohydrate derivative containing one or more sugar units and acylated in the C-1 and C-2 positions of the reducing sugar unit, the acyl groups in the C-1 and C-2 positions being different, is reacted with a alcohol or a thiol in the presence of a Lewis acid.
Claim 32
Dependent Claim
104 words
A method according to claim 27 in which the alcohol or thiol is selected from partially protected sugars and compounds of the type H--X--R--R' wherein X is oxygen or sulphur, R is selected from the group consisting of alkylene with up to 25 carbon atoms, alkylene with up to 25 carbon atoms with a carbon chain interrupted by a sulfur atom, or aryl, and R' is H, F, Cl, Br, I, CHO, CH(OR") 2 , NO 2 , NH 2 , OH, SH, COOH, COOCH 3 , COOCH 2 CH 3 , CONHNH 2 , or CON 3 wherein R" is C 1-4 alkyl.
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) | 1992-10-02 | 1993-04-03 | 1993-10-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-10-02 | 1997-04-03 | 1997-10-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2000-10-02 | 2001-04-03 | 2001-10-03 | $7700.00 | Window Closed / Lapsed |