Synthesis of branched-chain, pyrrolidino-sugar derivatives related to apiose
Identifieur interne : 001724 ( Main/Exploration ); précédent : 001723; suivant : 001725Synthesis of branched-chain, pyrrolidino-sugar derivatives related to apiose
Auteurs : D. H. Ball [États-Unis] ; F. H. Bissett [États-Unis] ; M. H. Halford [États-Unis] ; L. Long Jr. [États-Unis]Source :
- Carbohydrate Research [ 0008-6215 ] ; 1975.
Abstract
3-C-(Acetamidomethyl)-1,2-O-isopropylidene-β-l-threofuranose (4) and the 3-acetate (5) have been prepared in high yields from mono-O-isopropylidene-d-apiose [3-C-(hydroxymethyl)-1,2-O-isopropylidene-β-l-threofuranose] (1). Acid-catalyzed methanolysis of 4 caused migration of the isopropylidene group and the formation of methyl 4-acetamido-4-deoxy-3-C-(hydroxymethyl)-2,3-O-isopropylidene-β-d-erythrofuranoside (8) in 25% yield. The major product (45%) from the acetolysis of 4 was also a pyrrolidine derivative, namely, 4-acetamido-3-C-(acetoxymethyl)-1-O-acetyl-4-deoxy-2,3-O-isopropylidene-β-d-erythrofuranose (10). Acetolysis of 5 removed the isopropylidene group and gave four acetylated pyrrolidines (isomeric at C-1 and C-2). Conditions which resulted in minimal epimerization at C-2 were established, and the major isomers 12 and 13 were isolated in reasonable yields. 1H- and 13C-n.m.r. data for equilibrium solutions of the pyrrolidines, and for intermediates 1-5, are given.
Url:
DOI: 10.1016/S0008-6215(00)85869-3
Affiliations:
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<record><TEI wicri:istexFullTextTei="biblStruct"><teiHeader><fileDesc><titleStmt><title xml:lang="en">Synthesis of branched-chain, pyrrolidino-sugar derivatives related to apiose</title><author><name sortKey="Ball, D H" sort="Ball, D H" uniqKey="Ball D" first="D. H." last="Ball">D. H. Ball</name></author><author><name sortKey="Bissett, F H" sort="Bissett, F H" uniqKey="Bissett F" first="F. H." last="Bissett">F. H. Bissett</name></author><author><name sortKey="Halford, M H" sort="Halford, M H" uniqKey="Halford M" first="M. H." last="Halford">M. H. Halford</name></author><author><name sortKey="Long Jr, L" sort="Long Jr, L" uniqKey="Long Jr L" first="L." last="Long Jr.">L. 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H." last="Ball">D. H. Ball</name><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Massachusetts</region></placeName><wicri:cityArea>Food Sciences Laboratory, U.S. Army Natick Development Center, Natick</wicri:cityArea></affiliation></author><author><name sortKey="Bissett, F H" sort="Bissett, F H" uniqKey="Bissett F" first="F. H." last="Bissett">F. H. Bissett</name><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Massachusetts</region></placeName><wicri:cityArea>Food Sciences Laboratory, U.S. Army Natick Development Center, Natick</wicri:cityArea></affiliation></author><author><name sortKey="Halford, M H" sort="Halford, M H" uniqKey="Halford M" first="M. H." last="Halford">M. H. Halford</name><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Massachusetts</region></placeName><wicri:cityArea>Food Sciences Laboratory, U.S. Army Natick Development Center, Natick</wicri:cityArea></affiliation></author><author><name sortKey="Long Jr, L" sort="Long Jr, L" uniqKey="Long Jr L" first="L." last="Long Jr.">L. Long Jr.</name><affiliation wicri:level="2"><country xml:lang="fr">États-Unis</country><placeName><region type="state">Massachusetts</region></placeName><wicri:cityArea>Food Sciences Laboratory, U.S. Army Natick Development Center, Natick</wicri:cityArea></affiliation></author></analytic><monogr></monogr><series><title level="j">Carbohydrate Research</title><title level="j" type="abbrev">CAR</title><idno type="ISSN">0008-6215</idno><imprint><publisher>ELSEVIER</publisher><date type="published" when="1975">1975</date><biblScope unit="volume">45</biblScope><biblScope unit="issue">1</biblScope><biblScope unit="page" from="91">91</biblScope><biblScope unit="page" to="103">103</biblScope></imprint><idno type="ISSN">0008-6215</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0008-6215</idno></seriesStmt></fileDesc><profileDesc><textClass></textClass><langUsage><language ident="en">en</language></langUsage></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">3-C-(Acetamidomethyl)-1,2-O-isopropylidene-β-l-threofuranose (4) and the 3-acetate (5) have been prepared in high yields from mono-O-isopropylidene-d-apiose [3-C-(hydroxymethyl)-1,2-O-isopropylidene-β-l-threofuranose] (1). Acid-catalyzed methanolysis of 4 caused migration of the isopropylidene group and the formation of methyl 4-acetamido-4-deoxy-3-C-(hydroxymethyl)-2,3-O-isopropylidene-β-d-erythrofuranoside (8) in 25% yield. The major product (45%) from the acetolysis of 4 was also a pyrrolidine derivative, namely, 4-acetamido-3-C-(acetoxymethyl)-1-O-acetyl-4-deoxy-2,3-O-isopropylidene-β-d-erythrofuranose (10). Acetolysis of 5 removed the isopropylidene group and gave four acetylated pyrrolidines (isomeric at C-1 and C-2). Conditions which resulted in minimal epimerization at C-2 were established, and the major isomers 12 and 13 were isolated in reasonable yields. 1H- and 13C-n.m.r. data for equilibrium solutions of the pyrrolidines, and for intermediates 1-5, are given.</div></front></TEI><affiliations><list><country><li>États-Unis</li></country><region><li>Massachusetts</li></region></list><tree><country name="États-Unis"><region name="Massachusetts"><name sortKey="Ball, D H" sort="Ball, D H" uniqKey="Ball D" first="D. H." last="Ball">D. H. Ball</name></region><name sortKey="Bissett, F H" sort="Bissett, F H" uniqKey="Bissett F" first="F. H." last="Bissett">F. H. Bissett</name><name sortKey="Halford, M H" sort="Halford, M H" uniqKey="Halford M" first="M. H." last="Halford">M. H. Halford</name><name sortKey="Long Jr, L" sort="Long Jr, L" uniqKey="Long Jr L" first="L." last="Long Jr.">L. Long Jr.</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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