Treatment of tri-O acetyl-D-glucal 1 with diverse thiols 2-7 in the presence of LiBF4 in CH3CN, furnished aryl/alkyl 2,3-unsaturated thioglycopyranosides 8-13 (56-72%).

Boga Sobhana Babu

Kalapattukuppuswamy Kuppuswamy B. Balasubramanian

acetonitrile

acid

glycoside

lithium derivative

natural product

thioglycoside

article

catalysis

catalyst

chemical modification

covalent bond

reaction analysis

stereochemistry

structure analysis

synthesis

IIT Madras is a public technical and research university located in Chennai, Tamil Nadu. Founded in 1959, it is recognised as an Institute of National Importance.

IIT Madras has been ranked as the top engineering institute in India for four years in a row by the National Institutional Ranking Framework of the MHRD

It currently offers undergraduate, postgraduate and research degrees across 16 disciplines in Engineering, Sciences, Humanities and Management. About 596 faculty belonging to science and engineering departments and centres of the Institute are engaged in teaching, research and industrial consultancy.

IIT Madras

Synthesis of 2,3-unsaturated thioglycopyranosides mediated by lithium tetrafluoroborate

Tetrahedron Letters

Journal of Applied Electrochemistry

Preparative scale synthesis ofO-glycosides and of a disaccharide by electrochemical oxidation of phenylS-glycosides

Journal of the American Chemical Society

The synthesis of the core trisaccharide of esperamicin: corroboration of the proposed structure for its rearrangement product and stabilization of the core trisaccharide domain

The Journal of Organic Chemistry

Regioselective synthesis of substituted 1-thiohex-2-enopyranosides

Synthetic Communications

Hydrolysis of Acetals and Ketals Using LiBF4

Chemistry of β-trimethylsilylethanol. II. A new method for protection of an anomeric center in pyranosides

Journal	Tetrahedron Letters
ISSN	00404039
Open Access	No