Syntheis of tri-O-benzyl-2-C-acetoxymethylglycals and subsequent Ferrier rearrangement to give 2-C-methylene glycosides is described.

Cannan Booma

Kalapattukuppuswamy Kuppuswamy B. Balasubramanian

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

A new ferrier system: 2-C-acetoxymethylglycals. A covenient entry to 2-C-methylene glycosides

Journal of the Chemical Society, Chemical Communications

Ozonolysis of 2-acetoxymethyl-1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-D- arabino-hex-1-enitol gave 1-O-acetyl-3,4,6-tri-O-benzyl-4-O-formyl-D-arabino- hex-2-ulose (5). Subsequent hydrolysis and acetylation of 5 provided 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-D-fructofuranose 6 in excellent yield. This methodology allows specific deuteration at C-1 of a protected D-fructofuranose derivative. This approach therefore could serve as [6+1-1] formulation for hexose series inter-conversion, that is, aldohexopyranose to ketohexofuranose. © 2005 Elsevier Ltd. All rights reserved.

Carbohydrate Research

Stereoselective synthesis of a ketohexofuranose from an aldohexopyranose by a [6+1-1] strategy

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

Tetrahedron Letters

Vilsmeier-haack reactoin of glycals-a short route to C-2-formyl glycals

Glycobiology

XVIth International Carbohydrate Symposium

Reactions of 3- -acetyl-2- - -tolylsulfonyl-D- - and - - -hex-1-enitol derivatives with nucleophiles; the SN2′ mechanism is proved firstly in glycal derivatives

General Carbohydrate Method

cis-1,2-Glycosides

Journal	Journal of the Chemical Society, Chemical Communications
ISSN	00224936
Open Access	No