PRODUCTS FROM FURANS .7. A GENERAL-ROUTE FOR THE SYNTHESIS OF ALPHA-(1,2-CIS) AND BETA-(1,2-TRANS) GLYCOCONJUGATES VIA 1-O-ACYL AND 1-O-ETHOXYCARBONYL-2-AZIDO-2,3-DIDEOXYGLYCOPYRANOSIDES
A methodology for the synthesis of 2,3,6-trideoxy- and 2,3-dideoxy-2-aminoglycosides is presented. 2,3-Dideoxyhex-2-enopyranos-4-uloses (named also as 2H-pyran-3(6H)-Ones) were used for the synthesis of 1-O-acetyl, 1-O-ethyloxycarbonyl and 1-S-phenyl-2,3,6-trideoxy-(or 2,3-dideoxy)-2-azidoglycopyran...
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| Published in | Journal of heterocyclic chemistry Vol. 28; no. 5; pp. 1325 - 1337 |
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| Main Authors | , |
| Format | Journal Article |
| Language | English |
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TAMPA
HETERO CORPORATION
01.08.1991
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| Abstract | A methodology for the synthesis of 2,3,6-trideoxy- and 2,3-dideoxy-2-aminoglycosides is presented. 2,3-Dideoxyhex-2-enopyranos-4-uloses (named also as 2H-pyran-3(6H)-Ones) were used for the synthesis of 1-O-acetyl, 1-O-ethyloxycarbonyl and 1-S-phenyl-2,3,6-trideoxy-(or 2,3-dideoxy)-2-azidoglycopyranosyl donors. Glycosidation of the above thio-ethers with a variety of alcohols in the presence of N-bromosuccinimide as activator yielded predominantly alpha-glycosides, while acetates afforded beta-glycosides when TMSOTf was used as a promoter. The coupling of carbonates using tin tetrachloride or TMSOTf proved to be the most successful procedure, yielding the beta-glycoside as the predominant product. Thus, glycoconjugates of aminosugars, steroids and aminoacids have been synthesized. |
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| AbstractList | A methodology for the synthesis of 2,3,6-trideoxy- and 2,3-dideoxy-2-aminoglycosides is presented. 2,3-Dideoxyhex-2-enopyranos-4-uloses (named also as 2H-pyran-3(6H)-Ones) were used for the synthesis of 1-O-acetyl, 1-O-ethyloxycarbonyl and 1-S-phenyl-2,3,6-trideoxy-(or 2,3-dideoxy)-2-azidoglycopyranosyl donors. Glycosidation of the above thio-ethers with a variety of alcohols in the presence of N-bromosuccinimide as activator yielded predominantly alpha-glycosides, while acetates afforded beta-glycosides when TMSOTf was used as a promoter. The coupling of carbonates using tin tetrachloride or TMSOTf proved to be the most successful procedure, yielding the beta-glycoside as the predominant product. Thus, glycoconjugates of aminosugars, steroids and aminoacids have been synthesized. |
| Author | GEORGIADIS, MP COULADOUROS, EA |
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| References | PAULSEN, H (WOS:A1984ABM3600005) 1984; 135 GONZALEZ, F (WOS:A1975AJ65700008) 1975; 42 Montreuil, J (MEDLINE:6996449) 1980; 37 GEORGIADIS, MP (WOS:A1986D210900020) 1986; 51 GEORGIADIS, MP (WOS:A1988P116500056) 1988; 25 MARTIN, SF (WOS:A1988N993500012) 1988; 44 JANSSON, K (WOS:A1988R227700006) 1988; 53 GEORGIADIS M (WOS:A1991HU84500026.5) 1983 FLORENT, JC (WOS:A1987J558200024) 1987 USUI, T (WOS:A1988M732700013) 1988; 174 SAKAKIBARA, T (WOS:A1977DY58900005) 1977; 58 HAKOMORI S (WOS:A1991HU84500026.14) 1976; 7 INABA, S (WOS:A1973P099200086) 1973; 95 PAULSEN H (WOS:A1991HU84500026.30) 1988 ITO, Y (WOS:A1988M470600026) 1988; 29 LEBOUL J (WOS:A1991HU84500026.22) 1977 OGAWA, T (WOS:A1981LY73200019) 1981; 93 HUGHES RC (WOS:A1991HU84500026.17) 1976 GEOFFREY MW (WOS:A1991HU84500026.4) 1986; 4 HOROWITZ MJ (WOS:A1991HU84500026.16) 1978; 2 GEORGIADIS, MP (WOS:A1976BD35600033) 1976; 19 JIN, H (WOS:A1983RK35900034) 1983; 61 GEORGIADIS MP (WOS:A1991HU84500026.7) 1988; 17 HOLDER, NL (WOS:A1982PC37200003) 1982; 82 GEORGIADIS MP (WOS:A1991HU84500026.6) 1983; 12 RINEHART KL (WOS:A1991HU84500026.31) 1980 NICOLAOU, KC (WOS:A1983QL86500054) 1983; 105 GEORGIADIS, MP (WOS:A1982NZ83300005) 1982; 47 ZAMOJSKI, A (WOS:A1982PX32500001) 1982; 40 GEORGIADIS, MP (WOS:A1986C410700060) 1986; 23 PAULSEN, H (WOS:A1980KE41100004) 1980; 113 PAULSEN, H (WOS:A1978FE17700027) 1978; 111 CHATANI, N (WOS:A1988P237400059) 1988; 53 BOIVIN, J (WOS:A1978ER65900003) 1978 |
| References_xml | – start-page: 965 year: 1977 ident: WOS:A1991HU84500026.22 publication-title: TETRAHEDRON contributor: fullname: LEBOUL J – volume: 105 start-page: 2430 year: 1983 ident: WOS:A1983QL86500054 article-title: A MILD AND GENERAL-METHOD FOR THE SYNTHESIS OF O-GLYCOSIDES publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: NICOLAOU, KC – volume: 51 start-page: 2725 year: 1986 ident: WOS:A1986D210900020 article-title: PRODUCTS FROM FURANS .4. SELECTIVE OXIDATION OF 2-FURFURYL ALCOHOL DERIVATIVES, IN THE PRESENCE OF ARYL THIOETHERS, WITH N-BROMOSUCCINIMIDE (NBS) - A NEW PROCEDURE FOR THE PREPARATION OF 2H-PYRAN-3(6H)-ONES publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: GEORGIADIS, MP – volume: 135 start-page: 53 year: 1984 ident: WOS:A1984ABM3600005 article-title: LEWIS ACID-CATALYZED SYNTHESES OF DI-SACCHARIDE AND TRI-SACCHARIDE SEQUENCES OF O-GLYCOPROTEINS AND N-GLYCOPROTEINS - USE OF TRIMETHYLSILYLTRIFLUORO-METHANE-SULFONATE publication-title: CARBOHYDRATE RESEARCH contributor: fullname: PAULSEN, H – volume: 61 start-page: 2442 year: 1983 ident: WOS:A1983RK35900034 article-title: ON THE SYNTHESIS OF CARDIOACTIVE STEROID GLYCOSIDES - ON CARDIOACTIVE STEROIDS .11. publication-title: CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE contributor: fullname: JIN, H – volume: 53 start-page: 5629 year: 1988 ident: WOS:A1988R227700006 article-title: 2-(TRIMETHYLSILYL)ETHYL GLYCOSIDES .3. SYNTHESIS, ANOMERIC DEBLOCKING, AND TRANSFORMATION INTO 1,2-TRANS 1-O-ACYL SUGARS publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: JANSSON, K – volume: 174 start-page: 133 year: 1988 ident: WOS:A1988M732700013 article-title: TOTAL SYNTHESIS OF NEOMYCIN-B publication-title: CARBOHYDRATE RESEARCH contributor: fullname: USUI, T – start-page: 125 year: 1980 ident: WOS:A1991HU84500026.31 publication-title: ACS SYM SER contributor: fullname: RINEHART KL – volume: 44 start-page: 3171 year: 1988 ident: WOS:A1988N993500012 article-title: A CONCISE ROUTE TO A KEY INTERMEDIATE IN THE TOTAL SYNTHESES OF (+)-TIRANDAMYCIC ACID AND (-)-TIRANDAMYCIN-A publication-title: TETRAHEDRON contributor: fullname: MARTIN, SF – volume: 53 start-page: 3387 year: 1988 ident: WOS:A1988P237400059 article-title: CATALYTIC SILOXYMETHYLATION OF GLYCOSIDES BY THE HSIR3/CO/CO2(CO)8 REACTION - A NEW ENTRY TO C-GLYCOSYL COMPOUNDS publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: CHATANI, N – start-page: 3567 year: 1988 ident: WOS:A1991HU84500026.30 publication-title: TETRAHEDRON LETT contributor: fullname: PAULSEN H – volume: 7 start-page: 223 year: 1976 ident: WOS:A1991HU84500026.14 publication-title: INT REV SCI ORG CH 2 contributor: fullname: HAKOMORI S – volume: 40 start-page: 1 year: 1982 ident: WOS:A1982PX32500001 article-title: THE SYNTHESIS OF SUGARS FROM NON-CARBOHYDRATE SUBSTRATES publication-title: ADVANCES IN CARBOHYDRATE CHEMISTRY AND BIOCHEMISTRY contributor: fullname: ZAMOJSKI, A – volume: 47 start-page: 3054 year: 1982 ident: WOS:A1982NZ83300005 article-title: PRODUCTS FROM FURANS .3. CRYSTAL AND MOLECULAR-STRUCTURE, PROTON NUCLEAR MAGNETIC-RESONANCE, AND CONFORMATIONAL STUDIES OF 2-ARYL-SUBSTITUTED 2-METHYL-6-HYDROXY-2H-PYRAN-3(6H)-ONE DERIVATIVES publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: GEORGIADIS, MP – volume: 17 start-page: 245 year: 1988 ident: WOS:A1991HU84500026.7 publication-title: CHIM CHRON contributor: fullname: GEORGIADIS MP – volume: 25 start-page: 995 year: 1988 ident: WOS:A1988P116500056 article-title: PRODUCTS FROM FURANS .5. SYNTHESIS OF OXYGEN CONTAINING ISOSTERES OF SYMPATHOMIMETIC AMINES VIA 6-HYDROXY-2H-PYRAN-3(6H)-ONES AND THEIR CIS-PLATINUM(II) COMPLEXES publication-title: JOURNAL OF HETEROCYCLIC CHEMISTRY contributor: fullname: GEORGIADIS, MP – volume: 12 start-page: 45 year: 1983 ident: WOS:A1991HU84500026.6 publication-title: CHIM CHRON contributor: fullname: GEORGIADIS MP – volume: 4 start-page: 45 year: 1986 ident: WOS:A1991HU84500026.4 publication-title: J CELL SCI S contributor: fullname: GEOFFREY MW – start-page: 1111 year: 1978 ident: WOS:A1978ER65900003 article-title: NEW METHOD FOR GLYCOSIDATION OF 2,6-DIDEOXY HEXA-PYRANOSE publication-title: TETRAHEDRON LETTERS contributor: fullname: BOIVIN, J – year: 1976 ident: WOS:A1991HU84500026.17 publication-title: MEMBRANE GLYCOPROTEI contributor: fullname: HUGHES RC – volume: 23 start-page: 605 year: 1986 ident: WOS:A1986C410700060 article-title: PRODUCTS FROM FURANS .6. SYNTHESIS OF DIHYDRO-2-DISUBSTITUTED-2H-PYRAN-3(4H)-ONES, TETRAHYDRO-3-(AMINOMETHYL)-2-(P-METHOXYPHENYL)-2-METHYL-2H-PYRAN-3-OL DERIVATIVES AND 6-(P-METHOXYPHENYL-6-METHYL-7-OXA-1,3-DIAZASPIRO[4,5]DECANE-2,4-DIONE publication-title: JOURNAL OF HETEROCYCLIC CHEMISTRY contributor: fullname: GEORGIADIS, MP – volume: 2 year: 1978 ident: WOS:A1991HU84500026.16 publication-title: GLYCOCONJUGATES contributor: fullname: HOROWITZ MJ – volume: 82 start-page: 287 year: 1982 ident: WOS:A1982PC37200003 article-title: THE CHEMISTRY OF HEXENULOSES publication-title: CHEMICAL REVIEWS contributor: fullname: HOLDER, NL – start-page: 17 year: 1983 ident: WOS:A1991HU84500026.5 publication-title: BBALCAN CHEM DAYS contributor: fullname: GEORGIADIS M – volume: 37 start-page: 157 year: 1980 ident: MEDLINE:6996449 article-title: Primary structure of glycoprotein glycans: basis for the molecular biology of glycoproteins. publication-title: Advances in carbohydrate chemistry and biochemistry contributor: fullname: Montreuil, J – volume: 19 start-page: 346 year: 1976 ident: WOS:A1976BD35600033 article-title: PRODUCTS FROM FURANS .1. SYNTHESIS AND ANTICOCCIDIAL AND ANTIMICROBIAL ACTIVITY OF 5-AMINO-5,6-DIHYDRO-6-METHOXY-2-METHYL-2-(4'-BIPHENYLYL)-2H-PYRAN-3(4H)-ONES AND RELATED COMPOUNDS publication-title: JOURNAL OF MEDICINAL CHEMISTRY contributor: fullname: GEORGIADIS, MP – volume: 95 start-page: 2062 year: 1973 ident: WOS:A1973P099200086 article-title: SYNTHETIC STUDIES BY USE OF CARBONATES .4. NEW METHODS FOR SYNTHESIS OF GLYCOSYL COMPOUNDS BY USE OF 1-O-ARYLOXYCARBONYL SUGAR DERIVATIVES publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY contributor: fullname: INABA, S – volume: 42 start-page: 267 year: 1975 ident: WOS:A1975AJ65700008 article-title: CATALYSIS BY MERCURIC ION OF REACTIONS OF GLYCALS WITH WATER publication-title: CARBOHYDRATE RESEARCH contributor: fullname: GONZALEZ, F – volume: 113 start-page: 2616 year: 1980 ident: WOS:A1980KE41100004 article-title: BRANCHED-CHAIN SUGARS, .16. SYNTHESES OF GAROSAMINE-TYPE C-4-METHYL BRANCHED AMINO-SUGARS publication-title: CHEMISCHE BERICHTE-RECUEIL contributor: fullname: PAULSEN, H – volume: 111 start-page: 2334 year: 1978 ident: WOS:A1978FE17700027 article-title: BUILDING UNITS FOR OLIGOSACCHARIDES .9. STEREOSELECTIVE SYNTHESIS OF ALPHA-GLYCOSIDICALLY LINKED DISACCHARIDES AND OLIGOSACCHARIDES OF 2-AMINO-2-DEOXY-D-GLUCOPYRANOSE publication-title: CHEMISCHE BERICHTE-RECUEIL contributor: fullname: PAULSEN, H – volume: 93 start-page: C6 year: 1981 ident: WOS:A1981LY73200019 article-title: TRIMETHYLSILYL TRIFLUOROMETHANESULFONATE AS AN EFFECTIVE CATALYST FOR GLYCOSIDE SYNTHESIS publication-title: CARBOHYDRATE RESEARCH contributor: fullname: OGAWA, T – volume: 58 start-page: 39 year: 1977 ident: WOS:A1977DY58900005 article-title: STEREOCHEMISTRY OF NUCLEOPHILIC-ADDITION REACTIONS .4. ADDITION OF HYDRAZOIC ACID TO METHYL 6-O-BENZOYL-2,3-DIDEOXY-ALPHA-D-GLYCERO-HEX-2-ENOPYRANOSID-4-ULOSE publication-title: CARBOHYDRATE RESEARCH contributor: fullname: SAKAKIBARA, T – start-page: 1171 year: 1987 ident: WOS:A1987J558200024 article-title: STEREOCONTROLLED ROUTE TO 3-AMINO-2,3,6-TRIDEOXY-HEXOPYRANOSES - K-10 MONTMORILLONITE AS A GLYCOSIDATION REAGENT FOR ACOSAMINIDE SYNTHESIS publication-title: JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS contributor: fullname: FLORENT, JC – volume: 29 start-page: 1061 year: 1988 ident: WOS:A1988M470600026 article-title: NOVEL APPROACHES TO GLYCOSIDE SYNTHESIS - BENZENESELENENYL TRIFLATE AS A PROMOTER OF THIOGLYCOSIDES - A NEW METHOD FOR O-GLYCOSYLATION USING THIOGLYCOSIDES publication-title: TETRAHEDRON LETTERS contributor: fullname: ITO, Y |
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| Snippet | A methodology for the synthesis of 2,3,6-trideoxy- and 2,3-dideoxy-2-aminoglycosides is presented. 2,3-Dideoxyhex-2-enopyranos-4-uloses (named also as... |
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| Title | PRODUCTS FROM FURANS .7. A GENERAL-ROUTE FOR THE SYNTHESIS OF ALPHA-(1,2-CIS) AND BETA-(1,2-TRANS) GLYCOCONJUGATES VIA 1-O-ACYL AND 1-O-ETHOXYCARBONYL-2-AZIDO-2,3-DIDEOXYGLYCOPYRANOSIDES |
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