Synthesis of D-Galactopyranosylphosphonic and D-(Galactopyranosylmethyl)phosphonic Acids as Intermediates of Inhibitors of Galactosyltransferases

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60461373%3A22330%2F06%3A00017233" target="_blank" >RIV/60461373:22330/06:00017233 - 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

Synthesis of D-Galactopyranosylphosphonic and D-(Galactopyranosylmethyl)phosphonic Acids as Intermediates of Inhibitors of Galactosyltransferases

Original language description

Employing the Michaelis-Arbuzov reaction of 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-galactopyranose with triethyl phosphite and trimethylsilyl trifluoromethanesulfonate, alfa- and beta-D-galactopyranosylphosphonic acids were prepared in 33 and 28% yields, respectively. (alfa-D-Galactopyranosylmethyl)phosphonic acid was synthesized by a five-step route from 2,3,4,6-tetra-O-benzyl-D-galactopyranose in 52% overall yield. When tested against bovine &#945;-1,3- and &#946;-1,4-galactosyltransferases, all three compounds showed, at best, very poor inhibitions.

Czech name

Příprava D-galaktopyranosylfosfonové a D-(galaktopyranosylmethyl)fosfonové kyseliny jako intermediátů inhibitorů galaktosyltransferas

Czech description

Obě alfa- a beta-D-galaktopyranosylfosfonové kyseliny byly připraveny Michaelis-Arbuzovovou reakcí 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-galaktopyranosy s triethyl-fosfitem a trimethylsilyl-trifluormethansulfonátem v celkovém výtěžku 33 a 28 %. (alfa-D-Galaktopyranosylmethyl)fosfonová kyselina byla připravena pětistupňovou syntézou z 2,3,4,6-tetra-O-benzyl-D-galaktopyranosy ve výtěžku 52 %. Všechny tři sloučeniny byly velmi slabými inhibitory hovězí alfa-1,3- a beta-1,4-galaktosyltransferasy.

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%2F04%2F0355" target="_blank" >GA203/04/0355: Inhibitors of alfa(1-3) galactosyltransferases based on the natural donor matrix</a><br>

Continuities

Z - Vyzkumny zamer (s odkazem do CEZ)

Publication year

2006

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

71

Issue of the periodical within the volume

11-12

Country of publishing house

CZ - CZECH REPUBLIC

Number of pages

14

Pages from-to

1659-1672

UT code for WoS article

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EID of the result in the Scopus database

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