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The rapid inactivation of erythromycin (Ery: 1) in gastric medium has led researchers at Roussel-Uclaf to develop roxithromycin (2) which contains at position C-9 an oxime whose hydroxyl is etherified by the (2-methoxyethoxy)methyl (MEM)group. The new semisynthetic macrolide exhibits satisfactory pharmacokinetics while retaining the antibacterial in vitro spectrum of erythromycin.x~4) We were interested to examine the influence of similar chemical modifications on the antibacterial properties of 16-membered macrolides and report here results related to tylosin (3).
ChemInformVolume 20, Issue 21 Reviews ChemInform Abstract: Fluorine-Labeled Antibiotics and Carbohydrates of Medical Interest L. H. BRITO BAPTISTELLA, L. H. BRITO BAPTISTELLA Inst. Chim. Subst. Nat., CNRS, 91190 Gif-sur-Yvette, Fr.Search for more papers by this authorS. CASTILLON, S. CASTILLON Inst. Chim. Subst. Nat., CNRS, 91190 Gif-sur-Yvette, Fr.Search for more papers by this authorA. DESSINGES, A. DESSINGES Inst. Chim. Subst. Nat., CNRS, 91190 Gif-sur-Yvette, Fr.Search for more papers by this authorR. FAGHIH, R. FAGHIH Inst. Chim. Subst. Nat., CNRS, 91190 Gif-sur-Yvette, Fr.Search for more papers by this authorG. LUKACS, G. LUKACS Inst. Chim. Subst. Nat., CNRS, 91190 Gif-sur-Yvette, Fr.Search for more papers by this authorA. OLESKER, A. OLESKER Inst. Chim. Subst. Nat., CNRS, 91190 Gif-sur-Yvette, Fr.Search for more papers by this authorTON THAT THANG TON THAT THANG, TON THAT THANG TON THAT THANG Inst. Chim. Subst. Nat., CNRS, 91190 Gif-sur-Yvette, Fr.Search for more papers by this author L. H. BRITO BAPTISTELLA, L. H. BRITO BAPTISTELLA Inst. Chim. Subst. Nat., CNRS, 91190 Gif-sur-Yvette, Fr.Search for more papers by this authorS. CASTILLON, S. CASTILLON Inst. Chim. Subst. Nat., CNRS, 91190 Gif-sur-Yvette, Fr.Search for more papers by this authorA. DESSINGES, A. DESSINGES Inst. Chim. Subst. Nat., CNRS, 91190 Gif-sur-Yvette, Fr.Search for more papers by this authorR. FAGHIH, R. FAGHIH Inst. Chim. Subst. Nat., CNRS, 91190 Gif-sur-Yvette, Fr.Search for more papers by this authorG. LUKACS, G. LUKACS Inst. Chim. Subst. Nat., CNRS, 91190 Gif-sur-Yvette, Fr.Search for more papers by this authorA. OLESKER, A. OLESKER Inst. Chim. Subst. Nat., CNRS, 91190 Gif-sur-Yvette, Fr.Search for more papers by this authorTON THAT THANG TON THAT THANG, TON THAT THANG TON THAT THANG Inst. Chim. Subst. Nat., CNRS, 91190 Gif-sur-Yvette, Fr.Search for more papers by this author First published: May 23, 1989 https://doi.org/10.1002/chin.198921329Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume20, Issue21May 23, 1989 RelatedInformation
AbstractThe protected deoxy‐α‐D‐threo‐hexopyranosidulose (I) reacts with trimethylsilyl cyanide (II) and ammonia (III) to give the α‐aminonitrile (IV) which is converted into the aldehyde (X) via the aziridine (VII) as outlined in the reaction scheme.
ChemInformVolume 18, Issue 39 Natural Products ChemInform Abstract: Synthesis of Derivatives of 3-Amino-2,2-difluoro-2,3,6-trideoxy-L-lyxopyranose (2,2-Difluorodaunosamine). A. DESSINGES, A. DESSINGES Inst. Chim. Subst. Nat., CNRS, 91190 Gif-sur-Yvette, FranceSearch for more papers by this authorF. C. ESCRIBANO, F. C. ESCRIBANO Inst. Chim. Subst. Nat., CNRS, 91190 Gif-sur-Yvette, FranceSearch for more papers by this authorG. LUKACS, G. LUKACS Inst. Chim. Subst. Nat., CNRS, 91190 Gif-sur-Yvette, FranceSearch for more papers by this authorA. OLESKER, A. OLESKER Inst. Chim. Subst. Nat., CNRS, 91190 Gif-sur-Yvette, FranceSearch for more papers by this authorT. T. THANG, T. T. THANG Inst. Chim. Subst. Nat., CNRS, 91190 Gif-sur-Yvette, FranceSearch for more papers by this author A. DESSINGES, A. DESSINGES Inst. Chim. Subst. Nat., CNRS, 91190 Gif-sur-Yvette, FranceSearch for more papers by this authorF. C. ESCRIBANO, F. C. ESCRIBANO Inst. Chim. Subst. Nat., CNRS, 91190 Gif-sur-Yvette, FranceSearch for more papers by this authorG. LUKACS, G. LUKACS Inst. Chim. Subst. Nat., CNRS, 91190 Gif-sur-Yvette, FranceSearch for more papers by this authorA. OLESKER, A. OLESKER Inst. Chim. Subst. Nat., CNRS, 91190 Gif-sur-Yvette, FranceSearch for more papers by this authorT. T. THANG, T. T. THANG Inst. Chim. Subst. Nat., CNRS, 91190 Gif-sur-Yvette, FranceSearch for more papers by this author First published: September 29, 1987 https://doi.org/10.1002/chin.198739303Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume18, Issue39September 29, 1987 RelatedInformation
Chemischer InformationsdienstVolume 17, Issue 19 Natural Products ChemInform Abstract: Synthesis of 2′-C-Fluoro-β-daunomycin (I). An Example of Configurational Retention in Fluorodehydroxylation with Diethylaminosulfur Trifluoride. S. CASTILLON, S. CASTILLONSearch for more papers by this authorA. DESSINGES, A. DESSINGESSearch for more papers by this authorR. FAGHIH, R. FAGHIHSearch for more papers by this authorG. LUKACS, G. LUKACSSearch for more papers by this authorA. OLESKER, A. OLESKERSearch for more papers by this authorT. T. THANG, T. T. THANGSearch for more papers by this author S. CASTILLON, S. CASTILLONSearch for more papers by this authorA. DESSINGES, A. DESSINGESSearch for more papers by this authorR. FAGHIH, R. FAGHIHSearch for more papers by this authorG. LUKACS, G. LUKACSSearch for more papers by this authorA. OLESKER, A. OLESKERSearch for more papers by this authorT. T. THANG, T. T. THANGSearch for more papers by this author First published: May 13, 1986 https://doi.org/10.1002/chin.198619321AboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinked InRedditWechat No abstract is available for this article. Volume17, Issue19May 13, 1986 RelatedInformation
The reaction of benzyl 2-benzamido-4,6-O-benzylidene-2-deoxy-3-O-tosyl-α-d-glucopyranoside or benzyl 4,6-O-benzylidene-2,3-benzoylepimino-2,3-dideoxy-α-d-allopyranoside with anhydrous tetrabutylammonium fluoride in hexamethylphosphoric triamide gave ∼40% of benzyl 3-benzamido-4,6-O-benzylidene-2,3-dideoxy-2-fluoro-α-d-altropyranoside (6a). Transformation of 6a into benzyl 3-benzamido-2,3,6-trideoxy-2-fluoro-α-d-arabino-hex-5-enopyranoside (13a) was carried out by well-established methodology. Hydrogenation of the double bond in 13a furnished the title compound in good yield. Methyl 3-benzamido-2,3,6-trideoxy-2-fluoro-β-l-galactopyranoside was also prepared in nine steps from 2-amino-2-deoxy-d-glucose.
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTSynthesis of 2'-C-.beta.-fluorodaunomycin. An example of configurational retention in fluorodehydroxylation with diethylaminosulfur trifluorideSergio Castillon, Aimee Dessinges, Ramine Faghih, Gabor Lukacs, Alain Olesker, and Ton That ThangCite this: J. Org. Chem. 1985, 50, 24, 4913–4917Publication Date (Print):November 1, 1985Publication History Published online1 May 2002Published inissue 1 November 1985https://pubs.acs.org/doi/10.1021/jo00224a052https://doi.org/10.1021/jo00224a052research-articleACS PublicationsRequest reuse permissionsArticle Views278Altmetric-Citations49LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InRedditEmail Other access optionsGet e-Alertsclose Get e-Alerts
ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTOxygen-17 NMR and oxygen-18-induced isotopic shifts in carbon-13 NMR for the elucidation of a controversial reaction mechanism in carbohydrate chemistryAimee Dessinges, Sergio Castillon, Alain Olesker, Ton That Thang, and Gabor LukacsCite this: J. Am. Chem. Soc. 1984, 106, 2, 450–451Publication Date (Print):January 1, 1984Publication History Published online1 May 2002Published inissue 1 January 1984https://doi.org/10.1021/ja00314a048RIGHTS & PERMISSIONSArticle Views253Altmetric-Citations19LEARN ABOUT THESE METRICSArticle Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated. Share Add toView InAdd Full Text with ReferenceAdd Description ExportRISCitationCitation and abstractCitation and referencesMore Options Share onFacebookTwitterWechatLinked InReddit PDF (295 KB) Get e-Alerts Get e-Alerts
An alternative synthesis of 3′-deoxy-3′-fluoro-d-ribofuranosyl nucleoside from d-arabinose is disclosed. Inversion of configuration at C3 on d-arabinoside promoted by DAST reagent is utilized to form lyxo-configured furanoside. After a sequence of fluorination, acidic methanolysis, triflation and displacement by -OBz. 3′-deoxy-3′-fluoro-d-ribofuranoside is obtained, which is then transformed to 1-O-benzoyl derivative. The synthesis of three 3′-deoxy-3′-fluoro-d-ribofuranosyl nucleosides, which can be served as fragment of antitumor active cyclic dinucleotide is finally completed through Vorbrüggen glycosylation .
L. Colombo, C. Scolastico, G. Lukacs, A. Dessinges, F. Aragozzini and C. Merendi, J. Chem. Soc., Chem. Commun., 1983, 1436 DOI: 10.1039/C39830001436
AbstractDie Substitution der 2‐Position von Hexopyranosen durch Fluor gelingt über ein geschütztes Glykosid, wie z.B. (Ic), und dessen Trifluormethansulfonsäureester (Id) (durch Behandeln des Alkohols mit dem Sulfonsäureanhydrid in wasserfreiem Pyridin bei ‐l0 °Cquantitativ erhältlich).