Chemischer InformationsdienstVolume 13, Issue 7 Natural Products ChemInform Abstract: SYNTHESIS OF 5-(4-CARBOXY-D-GALACTO-TETRITOL-1-YL)TETRAZOLE AND SOME OF ITS DERIVATIVES O. G. MARZOA, O. G. MARZOASearch for more papers by this authorI. M. E. THIEL, I. M. E. THIELSearch for more papers by this authorJ. O. DEFERRARI, J. O. DEFERRARISearch for more papers by this author O. G. MARZOA, O. G. MARZOASearch for more papers by this authorI. M. E. THIEL, I. M. E. THIELSearch for more papers by this authorJ. O. DEFERRARI, J. O. DEFERRARISearch for more papers by this author First published: February 16, 1982 https://doi.org/10.1002/chin.198207297AboutPDF 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. Volume13, Issue7February 16, 1982 RelatedInformation

The synthesis and mass spectra of some 2-methyl- and 2-phenyl-5-(polyacetoxyalkyl)-1,3,4-oxadiazoles (4-9) are described. The preferred conformations of 4-9 in solution have been determined by p.m.r. spectroscopy.

1,2,6,2′,3′,4′,6′-hepta-O-benzoyl-β-cellobiose (1) was prepared and its structure ascertained. Ammonolysis of 1 gave 6-O-benzoylcellobiose and cellobiose.

Synthesis of 5-(polyacetoxyalkyl)tetrazoles from some acetylated aldononitriles by reaction with ammonium azide is described. Deacetylation of these compounds afforded the corresponding 5-(polyhydroxyalkyl)tetrazoles.

This chapter discusses the reaction of ammonia with acyl esters of carbohydrates. The processes that take place in this reaction include migrations, degradations, transesterifications, and deacylations, and their simultaneous occurrence makes the interpretation of the whole scheme very difficult. The chapter provides a general description of the facts and a discussion of the different variables that play a role in the yield of products formed and in the mechanisms involved. The reaction of acyl esters of aldoses and aldobioses with ammonia consists of a set of competitive pathways—including intramolecular 0 →N migrations of acyl groups, deacylations, and transesterifications, with formation of “aldose amides” and variable proportions of the free sugar as the principal products. Examination of acyl derivatives indicates whether a cyclic or an acyclic structure is present. A table of derivatives in the chapter, enlists the yield and properties of the products isolated from the reaction of ammonia with acylated mono- and disaccharides.

This chapter discusses the methylation of diazomethane–boron trifluoride etherate. The use of diazomethane–boron trifluoride etherate reagent to methylate partially acylated sugars gives the methyl ethers of aldoses in yields between 70% and 90% and without acyl migration. The procedure is exemplified by the preparation of 2-O-methyl-d-mannose. methylating agents (3-5), frequently gives rise to acyl migration. In a 3-necked flask equipped with a stirrer and a thermometer, a few mg of d-mannose is added to 100 ml of acetic anhydride followed by 8 drops of 70% perchloric acid. To this yellow solution, 26.4 g of d-mannose is added portion-wise with continuous stirring during 20 min, while the temperature is kept at 40°–45°. Lastly, the solution is evaporated to dryness, and the residue (9.52 g) is crystallized and recrystallized from anhydrous ether.

4,6-Diaryl-2-(pyrrolidin-1-yl)-nicotinonitriles 2a–k and 3-amino-2,4-dicyano-5-aryl-biphenyls 3a–c were synthesized from 1,3-diaryl-prop-2-en-1-ones 1a–k and malononitrile by a convenient one-pot method. Likewise, the reaction of aromatic aldehydes with malononitrile afforded 6-amino-4-aryl-2-(pyrrolidin-1-yl)-pyridine-3,5-dicarbonitriles 6a–f. The reaction of mesityl oxide with malononitrile gave 5-amino-7-(pyrrolidin-1-yl)-2,4,4-trimethyl-1,4-dihydro-1,6-naphthyridine-8-carbonitrile 8. The NLO studies of the pyridinedinitrile derivatives 6a, b, f showed a high value while that of nicotinonitrile 2b was weak.

Penta-O-nicotinoyl-α-D-glucopyranose reacts with aqueous ammonia to yield N-nicotinoyl-D-glucofuranosylamine, 1-deoxy-1,1-bis(nicotinamido)-D-glucitol, and 2-(D-arabino-tetrahydroxybutyl)-6-(D-erythro-2,3,4-trihydroxybutyl)pyrazine. The structure of these compounds was ascertained by use of oxidation techniques and spectroscopic data. The formation of the pyrazine compound is discussed.

Publisher Summary This chapter discusses l,l-bis(acylamido)-l-deoxyalditols, which were first prepared by reaction of ammonia and silver oxide with acetylated aldononitriles. Synthesis of l,l-bis(acylamido)-l-deoxyalditols from acylated cyclic aldoses is also discussed. Tetra-O-acetyl-β- d -ribose is dissolved in 300 ml of 16% methanolic ammonia. The solution is left 24 hours at ∼25° and then evaporated to dryness under diminished pressure. The well-dried residue is extracted three times with ethyl acetate, dried again, and dissolved in 25 ml of absolute ethanol. The solution is evaporated slowly at ∼ 25°. Whereas for octa-O-benzoyl-β-maltose, maltose is suspended in 250 ml of pyridine, and 100 ml of benzoyl chloride is added to the suspension in portions, shaking the mixture and keeping it in a water and ice bath for 1 hour and then at ∼ 25° for 4 days.

AbstractAmmonolyse der Penta‐O‐acetyl‐β‐D‐mannopyranose (I) mit 25%igem Ammoniak (24 Stdn. bei Zimmertemperatur) ergibt 1,2‐Bis‐(acetamido)‐1‐desoxy‐D‐ mannit (29% Ausbeute) und nach Chromatographie der Mutterlauge an Cellulose N‐Acetyl‐α‐D‐glucofuranosylamin (II), N‐Acetyl‐β‐D‐mannofuranosylamin (III) und in 4%iger Ausbeute N‐Acetyl‐α‐D‐mannopyranosylamin (IV).

The factors that determine the favored formation of furanoid rings in the N-acylglycosylamines obtained by ammonolysis of O-acyl derivatives of some monosaccharides are discussed. The isolation and structure of N-acetyl-α- and -β-D-mannofuranosylamine, Nacetyl-α-D- mannopyranosylamine, N-acetyl-α-L-rhamnopyranosylamine, and Nacetyl-α-L-rhamnofuranosylamine are reported, and the conformation of the last two compounds is discussed on the basis of data from n.m.r. spectroscopy.

The reaction of d-gluconamide with benzoyl chloride and pyridine gave a complex mixture from which ethyl or methyl 2,3,5,6-tetra-O-benzoyl-d-gluconate (5 and 6) crystallized after treatment with ethanol or methanol, respectively. These esters were formed by alcoholysis of 2,3,5,6-tetra-O-benzoyl-d-glucono-1,4-lactone (4), which was isolated by column chromatography, together with penta-O-benzoyl-d-glucononitrile (7), penta-O-benzoyl-d-gluconamide (8), N-benzoyl-penta-O-benzoyl-d-gluconamide (9), and benzamide when an excess of benzoyl chloride was used. The isolation of 4 and benzamide was explained by the formation and hydrolysis of a benzoylated imino-lactone intermediate (3).

The conformational and steric factors that determine the different contributions of the acyl groups to the formation of 1,1-bis(acylamido)-1-deoxyalditols by the ammonolysis of acyl esters of carbohydrates of different structures are discussed. The isolation and structure of N-acetyl β-D-galactofuranosylamine, obtained by such a reaction, are reported, and the conformation of this sugar and that of the N-acetyl-α-D-glucofuranosylamine previously described are considered on the basis of n.m.r. data.

ADVERTISEMENT RETURN TO ISSUEPREVArticleNEXTThe Reaction of Ammonia with Acylated Disaccharides. V. The Wohl Reaction with Octa-O-acetylcellobionic Acid NitrileJorge O. Deferrari, María Elena Gelpi, and Raúl A. CadenasCite this: J. Org. Chem. 1965, 30, 7, 2328–2330Publication Date (Print):July 1, 1965Publication History Published online1 May 2002Published inissue 1 July 1965https://pubs.acs.org/doi/10.1021/jo01018a050https://doi.org/10.1021/jo01018a050research-articleACS PublicationsRequest reuse permissionsArticle Views31Altmetric-Citations6LEARN 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 ISSUEPREVArticleNEXTThe Reaction of Ammonia with Acylated Disaccharides. I. Acetyl Derivatives of CellobioseJorge O. Deferrari and Raúl A. CadenasCite this: J. Org. Chem. 1963, 28, 4, 1070–1072Publication Date (Print):April 1, 1963Publication History Published online1 May 2002Published inissue 1 April 1963https://pubs.acs.org/doi/10.1021/jo01039a049https://doi.org/10.1021/jo01039a049research-articleACS PublicationsRequest reuse permissionsArticle Views68Altmetric-Citations7LEARN 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