Confirmation of the structure of a glucono-1,4-lactone derivative obtained from silylation of glucono-1,5-lactone

P V  Murphy; C  McDonnell; L  Hamig; D E  Paterson; R J K  Taylor

Confirmation of the structure of a glucono-1,4-lactone derivative obtained from silylation of glucono-1,5-lactone

P V Murphy, C McDonnell, L Hamig, D E Paterson, R J K Taylor

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

Silylation reactions of glucono-1,5-lactone can give the persilylated glucono-1,5-lactone or the persilylated 1,4-lactone depending on the reaction conditions employed. The structure of 2,3,5,6-tetra-O-(tert-butyldimethylSilyl)-D-glucono-1,4-lactone, obtained in 84% yield from the reaction of glucono-1,5-lactone with TBSOTf and lutidine in dichloromethane, has been confirmed by X-ray crystallography. Formation of the glucono-1,5-lactone and manno-1,5-lactone derivatives and other possible products has also been ruled out by synthesis of possible exo-glycal derivatives of these lactones using the Ramberg-Backlund rearrangement of the corresponding sulfones. (C) 2003 Elsevier Science Ltd. All rights reserved.

Original language	English
Pages (from-to)	79-85
Number of pages	7
Journal	TETRAHEDRON-ASYMMETRY
Volume	14
Issue number	1
Publication status	Published - 6 Jan 2003

Keywords

EXO-GLYCALS

Cite this

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title = "Confirmation of the structure of a glucono-1,4-lactone derivative obtained from silylation of glucono-1,5-lactone",

abstract = "Silylation reactions of glucono-1,5-lactone can give the persilylated glucono-1,5-lactone or the persilylated 1,4-lactone depending on the reaction conditions employed. The structure of 2,3,5,6-tetra-O-(tert-butyldimethylSilyl)-D-glucono-1,4-lactone, obtained in 84% yield from the reaction of glucono-1,5-lactone with TBSOTf and lutidine in dichloromethane, has been confirmed by X-ray crystallography. Formation of the glucono-1,5-lactone and manno-1,5-lactone derivatives and other possible products has also been ruled out by synthesis of possible exo-glycal derivatives of these lactones using the Ramberg-Backlund rearrangement of the corresponding sulfones. (C) 2003 Elsevier Science Ltd. All rights reserved.",

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TY - JOUR

T1 - Confirmation of the structure of a glucono-1,4-lactone derivative obtained from silylation of glucono-1,5-lactone

AU - Murphy, P V

AU - McDonnell, C

AU - Hamig, L

AU - Paterson, D E

AU - Taylor, R J K

PY - 2003/1/6

Y1 - 2003/1/6

N2 - Silylation reactions of glucono-1,5-lactone can give the persilylated glucono-1,5-lactone or the persilylated 1,4-lactone depending on the reaction conditions employed. The structure of 2,3,5,6-tetra-O-(tert-butyldimethylSilyl)-D-glucono-1,4-lactone, obtained in 84% yield from the reaction of glucono-1,5-lactone with TBSOTf and lutidine in dichloromethane, has been confirmed by X-ray crystallography. Formation of the glucono-1,5-lactone and manno-1,5-lactone derivatives and other possible products has also been ruled out by synthesis of possible exo-glycal derivatives of these lactones using the Ramberg-Backlund rearrangement of the corresponding sulfones. (C) 2003 Elsevier Science Ltd. All rights reserved.

AB - Silylation reactions of glucono-1,5-lactone can give the persilylated glucono-1,5-lactone or the persilylated 1,4-lactone depending on the reaction conditions employed. The structure of 2,3,5,6-tetra-O-(tert-butyldimethylSilyl)-D-glucono-1,4-lactone, obtained in 84% yield from the reaction of glucono-1,5-lactone with TBSOTf and lutidine in dichloromethane, has been confirmed by X-ray crystallography. Formation of the glucono-1,5-lactone and manno-1,5-lactone derivatives and other possible products has also been ruled out by synthesis of possible exo-glycal derivatives of these lactones using the Ramberg-Backlund rearrangement of the corresponding sulfones. (C) 2003 Elsevier Science Ltd. All rights reserved.

KW - EXO-GLYCALS

M3 - Article

SN - 0957-4166

VL - 14

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EP - 85

JO - TETRAHEDRON-ASYMMETRY

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ER -