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

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22330%2F08%3A00019956" target="_blank" >RIV/60461373:22330/08:00019956 - isvavai.cz</a>

Result on the web

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DOI - Digital Object Identifier

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Result language

angličtina

Original language name

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

Original language 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.

Czech name

Stereoselektívní příprava 2,3-dideoxy-3-C-[(?-D-galactopyranosyl)methyl]- D-arabino-hexopyranosy and 2,3-dideoxy-3-C-[(?-D-galactopyranosyl)methyl]- L-arabino-hexopyranosy

Czech description

Diasteroisomérní deriváty substituovaného 2H-dihydropyranu 2b a 3b, získané po stereoselektivní cykloadicii (E)-4-(tetra-O-benzyl-?-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.

Type

J_x - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)

CEP classification

CC - Organic chemistry

OECD FORD branch

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Project

<a href="/en/project/GA203%2F08%2F1124" target="_blank" >GA203/08/1124: Stereoselective synthesis of disaccharide mimics as non-hydrolysable epitopes of vital glycoconjugates</a><br>

Continuities

Z - Vyzkumny zamer (s odkazem do CEZ)

Publication year

2008

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

Collection of Czechoslovak Chemical Communications

ISSN

0010-0765

e-ISSN

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Volume of the periodical

73

Issue of the periodical within the volume

5

Country of publishing house

CZ - CZECH REPUBLIC

Number of pages

11

Pages from-to

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UT code for WoS article

000258146300010

EID of the result in the Scopus database

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