About: A concise synthesis of 4-nitrophenyl 2-azido-2-deoxy- and 2-acetamido-2-deoxy-D-mannopyranosides

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About: A concise synthesis of 4-nitrophenyl 2-azido-2-deoxy- and 2-acetamido-2-deoxy-D-mannopyranosides Goto Sponge NotDistinct Permalink

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
Description	4-Nitrophenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha- and beta-D-mannopyranosides were prepared from methyl 4,6-O-benzylidene-alpha-D-glucopyranoside and 1,3,4,6-tetra-O-acetyl-alpha-D-glucopyranose, respectively. Chemoselective reduction of both azides with hydrogen sulfide readily afforded 4-nitrophenyl 2-acetamido-4,6-di-O-acetyl-2-deoxy-alpha-D- and -beta-D-mannopyranosides in higher yields than reduction with triphenylphosphine or a polymer-supported triarylphosphine. Subsequent de-O-acetylation yielded 4-nitrophenyl 2-acetamido-2-deoxy-alpha-D-mannopyranoside and 4-nitrophenyl 2-acetamido-2-deoxy-beta-D-mannopyranoside in 20 % and 44 % overall yields, respectively. 4-Nitrophenyl 3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha- and beta-D-mannopyranosides were prepared from methyl 4,6-O-benzylidene-alpha-D-glucopyranoside and 1,3,4,6-tetra-O-acetyl-alpha-D-glucopyranose, respectively. Chemoselective reduction of both azides with hydrogen sulfide readily afforded 4-nitrophenyl 2-acetamido-4,6-di-O-acetyl-2-deoxy-alpha-D- and -beta-D-mannopyranosides in higher yields than reduction with triphenylphosphine or a polymer-supported triarylphosphine. Subsequent de-O-acetylation yielded 4-nitrophenyl 2-acetamido-2-deoxy-alpha-D-mannopyranoside and 4-nitrophenyl 2-acetamido-2-deoxy-beta-D-mannopyranoside in 20 % and 44 % overall yields, respectively. (en)
Title	A concise synthesis of 4-nitrophenyl 2-azido-2-deoxy- and 2-acetamido-2-deoxy-D-mannopyranosides A concise synthesis of 4-nitrophenyl 2-azido-2-deoxy- and 2-acetamido-2-deoxy-D-mannopyranosides (en)
skos:prefLabel	A concise synthesis of 4-nitrophenyl 2-azido-2-deoxy- and 2-acetamido-2-deoxy-D-mannopyranosides A concise synthesis of 4-nitrophenyl 2-azido-2-deoxy- and 2-acetamido-2-deoxy-D-mannopyranosides (en)
skos:notation	RIV/60461373:22330/05:00022123!RIV10-MSM-22330___
http://linked.open...avai/riv/aktivita	P Z
http://linked.open...avai/riv/aktivity	P(GA203/01/1018), Z(MSM6046137305)
http://linked.open...iv/cisloPeriodika	1
http://linked.open...vai/riv/dodaniDat	2010
http://linked.open...aciTvurceVysledku	Hlaváčková, Martina Moravcová, Jitka Kefurt, Karel Popelová, Alena
http://linked.open.../riv/druhVysledku	J - Článek v odborném periodiku
http://linked.open...iv/duvernostUdaju	S - Úplné a pravdivé údaje nepodléhající ochraně podle zvláštních právních předpisů
http://linked.open...titaPredkladatele	Vysoká škola chemicko-technologická v Praze / Fakulta potravinářské a biochemické technologie
http://linked.open...dnocenehoVysledku	510809
http://linked.open...ai/riv/idVysledku	RIV/60461373:22330/05:00022123
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	2-azido-2-deoxymannoside; 2-acetamido-2-deoxymannopyranoside; 4-nitrophenyl glycoside; migration of acetyl group (en)
http://linked.open.../riv/klicoveSlovo	2-acetamido-2-deoxymannopyranoside 2-azido-2-deoxymannoside 4-nitrophenyl glycoside migration of acetyl group
http://linked.open...odStatuVydavatele	BE - Belgické království
http://linked.open...ontrolniKodProRIV	[549CB7D434BE]
http://linked.open...i/riv/nazevZdroje	Carbohydrate Research
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	4 (xsd:int)
http://linked.open...cetTvurcuVysledku	4 (xsd:int)
http://linked.open...vavai/riv/projekt	New enzymes and methods for chemoenzymatic synthesis of bioactive glycosides
http://linked.open...UplatneniVysledku	2005
http://linked.open...v/svazekPeriodika	340
http://linked.open...iv/tvurceVysledku	Moravcová, Jitka Kefurt, Karel Hlaváčková, Martina Popelová, Alena
http://linked.open...ain/vavai/riv/wos	000226538800020
http://linked.open...n/vavai/riv/zamer	Teoretické základy potravinářských a biochemických technologií
issn	0008-6215
number of pages	6 (xsd:int)
http://localhost/t...ganizacniJednotka	22330
is http://linked.open...avai/riv/vysledek of	A concise synthesis of 4-nitrophenyl 2-azido-2-deoxy- and 2-acetamido-2-deoxy-D-mannopyranosides

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