Towards inhibitors of glycosyltransferases: A novel approach to the synthesis of 3-acetamido-3-deoxy-D-psicofuranose derivatives

A novel synthetic strategy leading to 3-acetamido-3-deoxy-D-psicofuranose 9 is presented. The latter compound, after some manipulations, was transformed into fully protected 3-acetamido-3-deoxy-D-psicofuranose 11 as a potential substrate for the synthesis of N-acetylglucosaminyltransferase inhibitor...

Full description

Bibliographic Details
Main Authors:	Maroš Bella, Miroslav Koóš, Chun-Hung Lin
Format:	Article
Language:	English
Published:	Beilstein-Institut 2015-09-01
Series:	Beilstein Journal of Organic Chemistry
Subjects:	glycosyltransferases inhibitors D-psicofuranose synthesis thioglycosylation
Online Access:	https://doi.org/10.3762/bjoc.11.170

id	doaj-f9c067851d4243d993260bb59612fa2b
record_format	Article
spelling	doaj-f9c067851d4243d993260bb59612fa2b2021-02-02T03:25:47ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972015-09-011111547155210.3762/bjoc.11.1701860-5397-11-170Towards inhibitors of glycosyltransferases: A novel approach to the synthesis of 3-acetamido-3-deoxy-D-psicofuranose derivativesMaroš Bella0Miroslav Koóš1Chun-Hung Lin2Institute of Chemistry, Slovak Academy of Sciences, Dúbravská cesta 9, SK-845 38, Bratislava, SlovakiaInstitute of Chemistry, Slovak Academy of Sciences, Dúbravská cesta 9, SK-845 38, Bratislava, SlovakiaInstitute of Biological Chemistry, Academia Sinica, No. 128 Academia Road Sec. 2, Taipei 11529, TaiwanA novel synthetic strategy leading to 3-acetamido-3-deoxy-D-psicofuranose 9 is presented. The latter compound, after some manipulations, was transformed into fully protected 3-acetamido-3-deoxy-D-psicofuranose 11 as a potential substrate for the synthesis of N-acetylglucosaminyltransferase inhibitors designed by computational methods. After the attempted thioglycosylation of 11 with EtSH in the presence of BF3·OEt2, 2-methyloxazoline derivatives 13 and 14 were isolated.https://doi.org/10.3762/bjoc.11.170glycosyltransferasesinhibitorsD-psicofuranosesynthesisthioglycosylation
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Maroš Bella Miroslav Koóš Chun-Hung Lin
spellingShingle	Maroš Bella Miroslav Koóš Chun-Hung Lin Towards inhibitors of glycosyltransferases: A novel approach to the synthesis of 3-acetamido-3-deoxy-D-psicofuranose derivatives Beilstein Journal of Organic Chemistry glycosyltransferases inhibitors D-psicofuranose synthesis thioglycosylation
author_facet	Maroš Bella Miroslav Koóš Chun-Hung Lin
author_sort	Maroš Bella
title	Towards inhibitors of glycosyltransferases: A novel approach to the synthesis of 3-acetamido-3-deoxy-D-psicofuranose derivatives
title_short	Towards inhibitors of glycosyltransferases: A novel approach to the synthesis of 3-acetamido-3-deoxy-D-psicofuranose derivatives
title_full	Towards inhibitors of glycosyltransferases: A novel approach to the synthesis of 3-acetamido-3-deoxy-D-psicofuranose derivatives
title_fullStr	Towards inhibitors of glycosyltransferases: A novel approach to the synthesis of 3-acetamido-3-deoxy-D-psicofuranose derivatives
title_full_unstemmed	Towards inhibitors of glycosyltransferases: A novel approach to the synthesis of 3-acetamido-3-deoxy-D-psicofuranose derivatives
title_sort	towards inhibitors of glycosyltransferases: a novel approach to the synthesis of 3-acetamido-3-deoxy-d-psicofuranose derivatives
publisher	Beilstein-Institut
series	Beilstein Journal of Organic Chemistry
issn	1860-5397
publishDate	2015-09-01
description	A novel synthetic strategy leading to 3-acetamido-3-deoxy-D-psicofuranose 9 is presented. The latter compound, after some manipulations, was transformed into fully protected 3-acetamido-3-deoxy-D-psicofuranose 11 as a potential substrate for the synthesis of N-acetylglucosaminyltransferase inhibitors designed by computational methods. After the attempted thioglycosylation of 11 with EtSH in the presence of BF3·OEt2, 2-methyloxazoline derivatives 13 and 14 were isolated.
topic	glycosyltransferases inhibitors D-psicofuranose synthesis thioglycosylation
url	https://doi.org/10.3762/bjoc.11.170
work_keys_str_mv	AT marosbella towardsinhibitorsofglycosyltransferasesanovelapproachtothesynthesisof3acetamido3deoxydpsicofuranosederivatives AT miroslavkoos towardsinhibitorsofglycosyltransferasesanovelapproachtothesynthesisof3acetamido3deoxydpsicofuranosederivatives AT chunhunglin towardsinhibitorsofglycosyltransferasesanovelapproachtothesynthesisof3acetamido3deoxydpsicofuranosederivatives
_version_	1724307851777671168

Towards inhibitors of glycosyltransferases: A novel approach to the synthesis of 3-acetamido-3-deoxy-D-psicofuranose derivatives

Similar Items