About: Stereoselective preparation of 2,3-dideoxy-3-C-[(α-D-galactopyranosyl)methyl]- D-arabino-hexopyranose and 2,3-dideoxy-3-C-[(α-D-galactopyranosyl)methyl]- L-arabino-hexopyranose

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About: Stereoselective preparation of 2,3-dideoxy-3-C-[(α-D-galactopyranosyl)methyl]- D-arabino-hexopyranose and 2,3-dideoxy-3-C-[(α-D-galactopyranosyl)methyl]- L-arabino-hexopyranose Goto Sponge NotDistinct Permalink

An Entity of Type : http://linked.opendata.cz/ontology/domain/vavai/Vysledek, within Data Space : linked.opendata.cz associated with source document(s)

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rdf:type	skos:Concept http://linked.opendata.cz/ontology/domain/vavai/Vysledek
Description	The diastereomeric substituted 2H-dihydropyran derivatives 2b and 3b were obtained by the stereoselective cycloaddition of (E)-4-(tetra-O-benzyl-alpha-D-galactopyranosyl)-1-(thiazol-2-yl)but2-en-1-one (1) with either of the enantiomeric chiral vinyl ethers (R)-4 or (S)-4. Reduction of the ester group, transformation of the thiazole ring into an aldehyde group and reaction with an excess of borane afforded the final C-(1 - 3)-disaccharide structures. The obtained C-(1 - 3)-disaccharides, containing an L- or D-deoxy-arabino-hexopyranose moiety at the reducing end, were characterized as peracetylated methyl glycosides 9a, 9b and 12a, 12b. The diastereomeric substituted 2H-dihydropyran derivatives 2b and 3b were obtained by the stereoselective cycloaddition of (E)-4-(tetra-O-benzyl-alpha-D-galactopyranosyl)-1-(thiazol-2-yl)but2-en-1-one (1) with either of the enantiomeric chiral vinyl ethers (R)-4 or (S)-4. Reduction of the ester group, transformation of the thiazole ring into an aldehyde group and reaction with an excess of borane afforded the final C-(1 - 3)-disaccharide structures. The obtained C-(1 - 3)-disaccharides, containing an L- or D-deoxy-arabino-hexopyranose moiety at the reducing end, were characterized as peracetylated methyl glycosides 9a, 9b and 12a, 12b. (en) Diasteroisomérní deriváty substituovaného 2H-dihydropyranu 2b a 3b, získané po stereoselektivní cykloadicii (E)-4-(tetra-O-benzyl-α-D-galactopyranosyl)-1-(thiazol-2-yl)-but-2-en-1-onu 1 s oběma enantiomery chirálníhoi vinyletheru (R)-4 a (S)-4 byly po redukci esterové skupiny, transformaci thiazolového kruhu na aldehyd a reakci s nadbytkem boranu převedeny na finální struktury C-(1-3)-disacharidů. Získané C-(1-3)-disacharidy, obsahujíci na redukujícim konci deoxy-arabino-hexopyranosu, byly charakterizovány jako peracetylované methylglykosidy. (cs)
Title	Stereoselective preparation of 2,3-dideoxy-3-C-[(α-D-galactopyranosyl)methyl]- D-arabino-hexopyranose and 2,3-dideoxy-3-C-[(α-D-galactopyranosyl)methyl]- L-arabino-hexopyranose Stereoselective preparation of 2,3-dideoxy-3-C-[(α-D-galactopyranosyl)methyl]- D-arabino-hexopyranose and 2,3-dideoxy-3-C-[(α-D-galactopyranosyl)methyl]- L-arabino-hexopyranose (en) Stereoselektívní příprava 2,3-dideoxy-3-C-[(α-D-galactopyranosyl)methyl]- D-arabino-hexopyranosy and 2,3-dideoxy-3-C-[(α-D-galactopyranosyl)methyl]- L-arabino-hexopyranosy (cs)
skos:prefLabel	Stereoselective preparation of 2,3-dideoxy-3-C-[(α-D-galactopyranosyl)methyl]- D-arabino-hexopyranose and 2,3-dideoxy-3-C-[(α-D-galactopyranosyl)methyl]- L-arabino-hexopyranose Stereoselective preparation of 2,3-dideoxy-3-C-[(α-D-galactopyranosyl)methyl]- D-arabino-hexopyranose and 2,3-dideoxy-3-C-[(α-D-galactopyranosyl)methyl]- L-arabino-hexopyranose (en) Stereoselektívní příprava 2,3-dideoxy-3-C-[(α-D-galactopyranosyl)methyl]- D-arabino-hexopyranosy and 2,3-dideoxy-3-C-[(α-D-galactopyranosyl)methyl]- L-arabino-hexopyranosy (cs)
skos:notation	RIV/60461373:22330/08:00019956!RIV09-MSM-22330___
http://linked.open...avai/riv/aktivita	P Z
http://linked.open...avai/riv/aktivity	P(GA203/08/1124), Z(MSM6046137305)
http://linked.open...iv/cisloPeriodika	5
http://linked.open...vai/riv/dodaniDat	2009
http://linked.open...aciTvurceVysledku	Vích, Ondřej Kniežo, Ladislav Dvořáková, Hana
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	397459
http://linked.open...ai/riv/idVysledku	RIV/60461373:22330/08:00019956
http://linked.open...riv/jazykVysledku	eng - angličtina
http://linked.open.../riv/klicovaSlova	C-disaccharides; stereoselective synthesis; saccharide chemistry (en)
http://linked.open.../riv/klicoveSlovo	C-disaccharides saccharide chemistry stereoselective synthesis
http://linked.open...odStatuVydavatele	CZ - Česká republika
http://linked.open...ontrolniKodProRIV	[E482971B5509]
http://linked.open...i/riv/nazevZdroje	Collection of Czechoslovak Chemical Communications
http://linked.open...in/vavai/riv/obor	CC
http://linked.open...ichTvurcuVysledku	3 (xsd:int)
http://linked.open...cetTvurcuVysledku	4 (xsd:int)
http://linked.open...vavai/riv/projekt	Stereoselective synthesis of disaccharide mimics as non-hydrolysable epitopes of vital glycoconjugates
http://linked.open...UplatneniVysledku	2008
http://linked.open...v/svazekPeriodika	73
http://linked.open...iv/tvurceVysledku	Dvořáková, Hana Kniežo, Ladislav Parkan, Kamil Vích, Ondřej
http://linked.open...ain/vavai/riv/wos	000258146300010
http://linked.open...n/vavai/riv/zamer	Teoretické základy potravinářských a biochemických technologií
issn	0010-0765
number of pages	11 (xsd:int)
http://localhost/t...ganizacniJednotka	22330

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