PROCESS FOR STEROIDAL PERACYL GLYCOSIDES
A process for the synthesis of 1-O-steroidal-peracyl- beta -glycosides that provides greater beta -anomeric selectivity with reduced by-products and side reactions. The process comprises reacting heptaacyl-D-cellobiosyl-1-halide, tetraacyl-D-glucosyl-1-halide or tetraacyl-D-galactosyl-1-halide and a...
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| creator | BUSCH, FRANK, R GOGGIN, KATHLEEN, D SHINE, RUSSELL, J WALINSKY, STANLEY, W LAMBERT, JOHN, F |
| description | A process for the synthesis of 1-O-steroidal-peracyl- beta -glycosides that provides greater beta -anomeric selectivity with reduced by-products and side reactions. The process comprises reacting heptaacyl-D-cellobiosyl-1-halide, tetraacyl-D-glucosyl-1-halide or tetraacyl-D-galactosyl-1-halide and a trisubstituted silyl-3-O-steroid, wherein the steroid is tigogenin, hecogenin, 11-ketotigogenin, diosgenin, or cholesterol, in the presence of zinc fluoride under suitable conditions. Typically, the halide is bromide, chloride or fluoride, the acyl is alkanoyl(C1-C6), benzoyl or toluoyl and the silyl substitution is alkyl(C1-C6), phenyl or phenyl alkyl(C1-C6).
A process for the synthesis of 1-O-steroidal-peracyl-(beta)-glycosides that provides greater (beta)-anomeric selectivity with reduced by-products and side reactions. The process comprises reacting heptaacyl-D-cellobiosyl-1-halide, tetraacyl-D-glucosyl-1-halide or tetraacyl-D-galactosyl-1-halide and a trisubstituted silyl-3-O-steroid, wherein the steroid is tigogenin, hecogenin, 11-ketotigogenin, diosgenin, or cholesterol, in the presence of zinc fluoride under suitable conditions. Typically, the halide is bromide, chloride or fluoride, the acyl is alkanoyl(C1-C6), benzoyl or toluoyl and the silyl substitution is alkyl(C1-C6), phenyl or phenyl alkyl(C1-C6).
L'invention se rapporte à un processus de synthèse de beta-glycosides de péracyle 1-O-stéroïdiens qui produit une plus grande sélectivité beta-anomérique avec une réduction des sous-produits et des réactions secondaires. Le processus consiste à faire réagir heptaacyl-D-cellobiosyl-1-halogénure, tétraacyl-D-glucosyl-1-halogénure ou tétraacyl-D-galactosyl-1-halogénure et un sylil-3-O-stéroïde trisubstitué dans lequel le stéroïde représente titogénine, hécogénine, 11-cetotigogénine, diosgénine ou cholestérol en présence de fluorure de zinc dans des conditions appropriées. Généralement, l'halogénure est du bromure, chlorure ou fluorure, l'acyle représente alcanoyle (C1-C6), benzoyle ou toluoyle et la substitution silyle représente alkyle (C1-C6), phényle ou phénylalkyle (C1-C6). |
| format | Patent |
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A process for the synthesis of 1-O-steroidal-peracyl-(beta)-glycosides that provides greater (beta)-anomeric selectivity with reduced by-products and side reactions. The process comprises reacting heptaacyl-D-cellobiosyl-1-halide, tetraacyl-D-glucosyl-1-halide or tetraacyl-D-galactosyl-1-halide and a trisubstituted silyl-3-O-steroid, wherein the steroid is tigogenin, hecogenin, 11-ketotigogenin, diosgenin, or cholesterol, in the presence of zinc fluoride under suitable conditions. Typically, the halide is bromide, chloride or fluoride, the acyl is alkanoyl(C1-C6), benzoyl or toluoyl and the silyl substitution is alkyl(C1-C6), phenyl or phenyl alkyl(C1-C6).
L'invention se rapporte à un processus de synthèse de beta-glycosides de péracyle 1-O-stéroïdiens qui produit une plus grande sélectivité beta-anomérique avec une réduction des sous-produits et des réactions secondaires. Le processus consiste à faire réagir heptaacyl-D-cellobiosyl-1-halogénure, tétraacyl-D-glucosyl-1-halogénure ou tétraacyl-D-galactosyl-1-halogénure et un sylil-3-O-stéroïde trisubstitué dans lequel le stéroïde représente titogénine, hécogénine, 11-cetotigogénine, diosgénine ou cholestérol en présence de fluorure de zinc dans des conditions appropriées. Généralement, l'halogénure est du bromure, chlorure ou fluorure, l'acyle représente alcanoyle (C1-C6), benzoyle ou toluoyle et la substitution silyle représente alkyle (C1-C6), phényle ou phénylalkyle (C1-C6).</description><edition>5</edition><language>eng ; fre</language><subject>CHEMISTRY ; HUMAN NECESSITIES ; HYGIENE ; MEDICAL OR VETERINARY SCIENCE ; METALLURGY ; ORGANIC CHEMISTRY ; PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES ; STEROIDS</subject><creationdate>1994</creationdate><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://worldwide.espacenet.com/publicationDetails/biblio?FT=D&date=19940106&DB=EPODOC&CC=WO&NR=9400479A1$$EHTML$$P50$$Gepo$$Hfree_for_read</linktohtml><link.rule.ids>230,308,780,885,25555,76308</link.rule.ids><linktorsrc>$$Uhttps://worldwide.espacenet.com/publicationDetails/biblio?FT=D&date=19940106&DB=EPODOC&CC=WO&NR=9400479A1$$EView_record_in_European_Patent_Office$$FView_record_in_$$GEuropean_Patent_Office$$Hfree_for_read</linktorsrc></links><search><creatorcontrib>BUSCH, FRANK, R</creatorcontrib><creatorcontrib>GOGGIN, KATHLEEN, D</creatorcontrib><creatorcontrib>SHINE, RUSSELL, J</creatorcontrib><creatorcontrib>WALINSKY, STANLEY, W</creatorcontrib><creatorcontrib>LAMBERT, JOHN, F</creatorcontrib><title>PROCESS FOR STEROIDAL PERACYL GLYCOSIDES</title><description>A process for the synthesis of 1-O-steroidal-peracyl- beta -glycosides that provides greater beta -anomeric selectivity with reduced by-products and side reactions. The process comprises reacting heptaacyl-D-cellobiosyl-1-halide, tetraacyl-D-glucosyl-1-halide or tetraacyl-D-galactosyl-1-halide and a trisubstituted silyl-3-O-steroid, wherein the steroid is tigogenin, hecogenin, 11-ketotigogenin, diosgenin, or cholesterol, in the presence of zinc fluoride under suitable conditions. Typically, the halide is bromide, chloride or fluoride, the acyl is alkanoyl(C1-C6), benzoyl or toluoyl and the silyl substitution is alkyl(C1-C6), phenyl or phenyl alkyl(C1-C6).
A process for the synthesis of 1-O-steroidal-peracyl-(beta)-glycosides that provides greater (beta)-anomeric selectivity with reduced by-products and side reactions. The process comprises reacting heptaacyl-D-cellobiosyl-1-halide, tetraacyl-D-glucosyl-1-halide or tetraacyl-D-galactosyl-1-halide and a trisubstituted silyl-3-O-steroid, wherein the steroid is tigogenin, hecogenin, 11-ketotigogenin, diosgenin, or cholesterol, in the presence of zinc fluoride under suitable conditions. Typically, the halide is bromide, chloride or fluoride, the acyl is alkanoyl(C1-C6), benzoyl or toluoyl and the silyl substitution is alkyl(C1-C6), phenyl or phenyl alkyl(C1-C6).
L'invention se rapporte à un processus de synthèse de beta-glycosides de péracyle 1-O-stéroïdiens qui produit une plus grande sélectivité beta-anomérique avec une réduction des sous-produits et des réactions secondaires. Le processus consiste à faire réagir heptaacyl-D-cellobiosyl-1-halogénure, tétraacyl-D-glucosyl-1-halogénure ou tétraacyl-D-galactosyl-1-halogénure et un sylil-3-O-stéroïde trisubstitué dans lequel le stéroïde représente titogénine, hécogénine, 11-cetotigogénine, diosgénine ou cholestérol en présence de fluorure de zinc dans des conditions appropriées. Généralement, l'halogénure est du bromure, chlorure ou fluorure, l'acyle représente alcanoyle (C1-C6), benzoyle ou toluoyle et la substitution silyle représente alkyle (C1-C6), phényle ou phénylalkyle (C1-C6).</description><subject>CHEMISTRY</subject><subject>HUMAN NECESSITIES</subject><subject>HYGIENE</subject><subject>MEDICAL OR VETERINARY SCIENCE</subject><subject>METALLURGY</subject><subject>ORGANIC CHEMISTRY</subject><subject>PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES</subject><subject>STEROIDS</subject><fulltext>true</fulltext><rsrctype>patent</rsrctype><creationdate>1994</creationdate><recordtype>patent</recordtype><sourceid>EVB</sourceid><recordid>eNrjZNAICPJ3dg0OVnDzD1IIDnEN8vd0cfRRCHANcnSO9FFw94l09g_2dHEN5mFgTUvMKU7lhdLcDApuriHOHrqpBfnxqcUFicmpeakl8eH-liYGBibmlo6GxkQoAQDb3yQO</recordid><startdate>19940106</startdate><enddate>19940106</enddate><creator>BUSCH, FRANK, R</creator><creator>GOGGIN, KATHLEEN, D</creator><creator>SHINE, RUSSELL, J</creator><creator>WALINSKY, STANLEY, W</creator><creator>LAMBERT, JOHN, F</creator><scope>EVB</scope></search><sort><creationdate>19940106</creationdate><title>PROCESS FOR STEROIDAL PERACYL GLYCOSIDES</title><author>BUSCH, FRANK, R ; GOGGIN, KATHLEEN, D ; SHINE, RUSSELL, J ; WALINSKY, STANLEY, W ; LAMBERT, JOHN, F</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-epo_espacenet_WO9400479A13</frbrgroupid><rsrctype>patents</rsrctype><prefilter>patents</prefilter><language>eng ; fre</language><creationdate>1994</creationdate><topic>CHEMISTRY</topic><topic>HUMAN NECESSITIES</topic><topic>HYGIENE</topic><topic>MEDICAL OR VETERINARY SCIENCE</topic><topic>METALLURGY</topic><topic>ORGANIC CHEMISTRY</topic><topic>PREPARATIONS FOR MEDICAL, DENTAL, OR TOILET PURPOSES</topic><topic>STEROIDS</topic><toplevel>online_resources</toplevel><creatorcontrib>BUSCH, FRANK, R</creatorcontrib><creatorcontrib>GOGGIN, KATHLEEN, D</creatorcontrib><creatorcontrib>SHINE, RUSSELL, J</creatorcontrib><creatorcontrib>WALINSKY, STANLEY, W</creatorcontrib><creatorcontrib>LAMBERT, JOHN, F</creatorcontrib><collection>esp@cenet</collection></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext_linktorsrc</fulltext></delivery><addata><au>BUSCH, FRANK, R</au><au>GOGGIN, KATHLEEN, D</au><au>SHINE, RUSSELL, J</au><au>WALINSKY, STANLEY, W</au><au>LAMBERT, JOHN, F</au><format>patent</format><genre>patent</genre><ristype>GEN</ristype><title>PROCESS FOR STEROIDAL PERACYL GLYCOSIDES</title><date>1994-01-06</date><risdate>1994</risdate><abstract>A process for the synthesis of 1-O-steroidal-peracyl- beta -glycosides that provides greater beta -anomeric selectivity with reduced by-products and side reactions. The process comprises reacting heptaacyl-D-cellobiosyl-1-halide, tetraacyl-D-glucosyl-1-halide or tetraacyl-D-galactosyl-1-halide and a trisubstituted silyl-3-O-steroid, wherein the steroid is tigogenin, hecogenin, 11-ketotigogenin, diosgenin, or cholesterol, in the presence of zinc fluoride under suitable conditions. Typically, the halide is bromide, chloride or fluoride, the acyl is alkanoyl(C1-C6), benzoyl or toluoyl and the silyl substitution is alkyl(C1-C6), phenyl or phenyl alkyl(C1-C6).
A process for the synthesis of 1-O-steroidal-peracyl-(beta)-glycosides that provides greater (beta)-anomeric selectivity with reduced by-products and side reactions. The process comprises reacting heptaacyl-D-cellobiosyl-1-halide, tetraacyl-D-glucosyl-1-halide or tetraacyl-D-galactosyl-1-halide and a trisubstituted silyl-3-O-steroid, wherein the steroid is tigogenin, hecogenin, 11-ketotigogenin, diosgenin, or cholesterol, in the presence of zinc fluoride under suitable conditions. Typically, the halide is bromide, chloride or fluoride, the acyl is alkanoyl(C1-C6), benzoyl or toluoyl and the silyl substitution is alkyl(C1-C6), phenyl or phenyl alkyl(C1-C6).
L'invention se rapporte à un processus de synthèse de beta-glycosides de péracyle 1-O-stéroïdiens qui produit une plus grande sélectivité beta-anomérique avec une réduction des sous-produits et des réactions secondaires. Le processus consiste à faire réagir heptaacyl-D-cellobiosyl-1-halogénure, tétraacyl-D-glucosyl-1-halogénure ou tétraacyl-D-galactosyl-1-halogénure et un sylil-3-O-stéroïde trisubstitué dans lequel le stéroïde représente titogénine, hécogénine, 11-cetotigogénine, diosgénine ou cholestérol en présence de fluorure de zinc dans des conditions appropriées. Généralement, l'halogénure est du bromure, chlorure ou fluorure, l'acyle représente alcanoyle (C1-C6), benzoyle ou toluoyle et la substitution silyle représente alkyle (C1-C6), phényle ou phénylalkyle (C1-C6).</abstract><edition>5</edition><oa>free_for_read</oa></addata></record> |
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| title | PROCESS FOR STEROIDAL PERACYL GLYCOSIDES |
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