A Practical Silicon-Free Strategy for Differentiation of Hydroxy Groups in Arabinofuranose Derivatives

A Practical Silicon-Free Strategy for Differentiation of Hydroxy Groups in Arabinofuranose Derivatives Full article

Journal

Synthesis-Stuttgart
ISSN: 1437-210X , E-ISSN: 0039-7881

Output data

Year: 2012, Volume: 44, Number: 08, Pages: 1219-1225 Pages count : 7 DOI: 10.1055/s-0031-1290752

Authors

Abronina Polina ¹ , Podvalnyy Nikita ¹ , Sedinkin Sergey ¹ , Fedina Ksenia ^1,2 , Zinin Alexander ¹ , Chizhov Alexander ¹ , Torgov Vladimir ¹ , Kononov Leonid ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences
2	The Higher Chemical College of the Russian Academy of Sciences

Effective differentiation of 3,5-diol system and 2-hydroxy group in arabinofuranose derivatives, which is required for the preparation of building blocks useful for the synthesis of nucleoside analogues and oligosaccharide fragments of mycobacterial arabinogalactan and lipoarabinomannan, was achieved by using 3,5-di-O-benzoyl-1,2-O-benzylidene-β-d-arabinofuranose or 3-O-(chloroacetyl)-β-d-arabinofuranose 1,2,5-orthobenzoate, both readily accessible from inexpensive methyl α-d-arabinofuranoside via the corresponding glycosyl bromides. The use of expensive organosilicon protecting groups is completely avoided in this novel strategy, a feature that makes it amenable to scale-up.

Abronina P. , Podvalnyy N. , Sedinkin S. , Fedina K. , Zinin A. , Chizhov A. , Torgov V. , Kononov L.
A Practical Silicon-Free Strategy for Differentiation of Hydroxy Groups in Arabinofuranose Derivatives
Synthesis-Stuttgart. 2012. V.44. N08. P.1219-1225. DOI: 10.1055/s-0031-1290752 WOS Scopus OpenAlex

Web of science:	WOS:000303104400013
Scopus:	2-s2.0-84858711649
OpenAlex:	W2319145874

DB	Citing
OpenAlex	14
Scopus	16
Web of science	14