Length Matters: One Additional Methylene Group in a Reactant is Able to Affect the Reactivity Pattern and Significantly Increase the Product Yield

Length Matters: One Additional Methylene Group in a Reactant is Able to Affect the Reactivity Pattern and Significantly Increase the Product Yield Full article

Journal

Synlett
ISSN: 0936-5214 , E-ISSN: 1437-2096

Output data

Year: 2018, Volume: 29, Number: 15, Pages: 2043-2045 Pages count : 3 DOI: 10.1055/s-0037-1610648

Authors

Stepanova Elena V. ¹ , Podvalnyy Nikita M. ^1,2 , Abronina Polina I. ¹ , Kononov Leonid O. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences
2	Research School of Chemistry & Applied Biomedical Sciences, National Research Tomsk Polytechnic University

The outcome of the nucleophilic opening of 3-O-benzoyl-β-d-arabinofuranose 1,2,5-orthobenzoate with 4-(ω-chloroalkoxy)phenols (SnCl4, CH2Cl2, –25 °C) unusually strongly depends on the length of the methylene chain of the nucleophile. The presence of one extra methylene group in the molecule of 4-(3-chloropropoxy)phenol [as compared to 4-(2-chloroetoxy)phenol] results in four-fold reduction in the reaction time and five-fold increase in the yield of a selectively protected monosaccharide glycoside with a hydroxy group at C-5, which is a valuable building block for the synthesis of oligoarabinofuranosides related to mycobacterial arabinans. Possible reasons and consequences of this finding are discussed.

Stepanova E.V. , Podvalnyy N.M. , Abronina P.I. , Kononov L.O.
Length Matters: One Additional Methylene Group in a Reactant is Able to Affect the Reactivity Pattern and Significantly Increase the Product Yield
Synlett. 2018. V.29. N15. P.2043-2045. DOI: 10.1055/s-0037-1610648 WOS Scopus OpenAlex

Web of science:	WOS:000444457900019
Scopus:	2-s2.0-85053119868
OpenAlex:	W2887492949

DB	Citing
OpenAlex	19
Scopus	19
Web of science	19