http://rdf.ncbi.nlm.nih.gov/pubchem/patent/GB-950251-A
Outgoing Links
| Predicate | Object |
|---|---|
| assignee | http://rdf.ncbi.nlm.nih.gov/pubchem/patentassignee/MD5_966a6c1f382ec9bcb5e3839dfd73e5b8 |
| classificationCPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07H15-04 http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07H13-12 |
| classificationIPCInventive | http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07H15-04 http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07H13-12 |
| filingDate | 1962-01-26-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationDate | 1964-02-26-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| publicationNumber | GB-950251-A |
| titleOfInvention | Novel sugar derivatives and their manufacture |
| abstract | Glycosides of the general formula: <FORM:0950251/C2/1> wherein R is a nitro-phenyl or cyano-methyl group, and the two alkyl groups in the 5-position are identical with one another and the glycosido alkyl and aralkyl groups are C1-4- alkyl and monocyclic-aryl substituted C1-4-alkyl groups respectively and wherein the asterisks denote that the double bonds radiating from the carbon atoms so marked are appropriate to an alpha-glycoside, in particular methyl 5,5-dimethyl -4-(O methyl) -3- (O p-nitro-phenyloxycarbonyl) -2-(O benzoyl) -L- alphalyxopyranoside, are made by reacting the appropriate alkyl or aralkyl 5, 5-dialkyl -4- (O alkyl) -2- (O acyl) -L- lyxopyranoside with a chloroformic acid ester of the general formula: <FORM:0950251/C2/2> wherein R is a nitro-phenyl or cyano-methyl group, in the presence of a tertiary organic base. The preferred starting materials are methyl 5,5-dimethyl -4- (O methyl) -2- [O (benzoyl or p-methoxy-benzoyl)] -L- lyxopyranoside. The product may be converted to noviose by reaction with ammonia, hydrolysing the carbamoyl compound and de-etherifying it. The reactions are: <FORM:0950251/C2/3> Full details are also given for the preparation of the starting material from D-glucose, which undergoes the following transformations: 1, 2 mono-acetone derivative, tri-benzylate, hydrolyse off acetonyl group and methylate; acid catalysed hydrolysis yields the D-glucofuranose. This is oxidised to D-gamma gluconolactone; which is reacted with ammonia or methyl or dimethylamine to yield the D-gamma gluconic acid amide. The free hydroxyl group in the 4-position of the latter is esterified with a sulphonic acid; for example, by treatment with methane-sulphonic acid chloride. The next step consists in the solvolysis of the 2-(O alkyl)-3, 5, 6-tri (O benzyl) -D-gluconic acid amide which has been esterified in the 4-position with a sulphonic acid, whereupon a 2-(O-alkyl)-3, 5, 6-tri (O benzyl)-D-gamma-galactonolactone is formed. By reaction of this lactone with an alkylmagnesium halide by the Grignard method (preferably employing one mol of lactone to two mols of organo-metallic compound), followed by hydrolysis of the reaction product, a 1,1-dialkyl-2-(O-alkyl)-3, 5, 6-tri(O-benzyl) -D- galactonohexitol is obtained. The hydroxyl group in the 4-position of this hexitol is then esterified with benzoic acid or the appropriate alkyl- or alkoxy-substituted benzoic acid, or a functional derivative thereof. Preferred esterification agents are those which give the benzoyl or p-methoxy-benzoyl group. The esterification product is then reductively debenzylated and subjected to a glycol splitting reaction (employing, for example, lead tetraacetate in methylene chloride solution), whereupon a 5, 5-dialkyl -4- (O alkyl)2-(O acyl-L-lyxopyranose is formed. The latter is then acetalized with a C1-4-alkyl alcohol (which may contain a monocyclic aryl substituent) to form the required starting materials. The example includes full details of the synthesis of the starting material. |
| priorityDate | 1961-01-27-04:00^^<http://www.w3.org/2001/XMLSchema#date> |
| type | http://data.epo.org/linked-data/def/patent/Publication |
Incoming Links
Total number of triples: 49.