Kalapattukuppuswamy Kuppuswamy B. Balasubramanian

glycoside

article

priority journal

reaction 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

Reaction of 2,3-unsaturated aryl glycosides with lewis acids : a convenient entry to C-aryl glycosides

Tetrahedron Letters

Unusual behaviour of aryl 2-deoxy-D-galactosides under Lewis acid catalysis: A facile entry to C-aryl 2-deoxy-D-glycosides and bridged chiral benzopyran derivatives

A simple and convenient method for the synthesis of aryl-3,4,6-tri-O-benzyl-2-deoxy-2-methylene-hexopyranosides 5,6 and 7, glycosides which are not accessible by the conventional Ferrier rearrangement, has been described based on the Mitsunobu reaction of alcohols 3 and 4 with substituted phenols. The anomeric configurations of glycosides 5 and 6 were established by detailed NOE studies. The reaction is also successfully extended to the synthesis of phthaloyl derivative 10. A mild, neutral and non-acidic alternative to Ferrier rearrangement for the synthesis of 2,3-dideoxy-hex-2-enopyranosides has also been demonstrated with a variety of nucleophiles. © 1994.

Tetrahedron

Mitsunobu reaction of 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-2-hydroxymethyl-hex-1-enitols and 1,5-anhydro-2-deoxy-4,6-O-protected-hex-1-enitols. A novel method for the synthesis of 2-C-methylene glycosides and an useful alternative to Ferrier rearrangement

A short and facile entry to the 2, 3-unsaturated O-arylglyco sides via microwave induced Ferrier rearrangement of acetylated glucal is reported. © 1994, Taylor & Francis Group, LLC. All rights reserved.

Synthetic Communications

Microwave induced ferrier rearrangement

Reaction of 2,3-unsaturated aryl glycosides with Lewis acids : a convenient entry to C-aryl glycosides

Journal	Tetrahedron Letters
ISSN	00404039
Open Access	No