Rearrangement of derivatives of bis(ethylsulphonyl)-α-d-lyxopyranosylmethane

J. Grant Buchanan, Alan R. Edgar, Roderick J. Hutchison

Research output: Contribution to journalArticle

Abstract

Bis(ethylsulphonyl)(2,3-O-isopropylidene-a-d-lyxopyranosyl)methane (3) undergoes rearrangement in pyridine or methanolic sodium methoxide to give, at equilibrium, a mixture containing equal amounts of bis (ethylsulphonyl)-(2,3,O-iso-propylidene-a-d-lyxofuranosyl)methane (10), the corresponding ß-furanoid (12), and 3 itself. The rearrangement is completely suppressed by C-methylation of the bis(ethylsulphonyl) moiety. The mechanism of the MacDonald-Fischer degradation of bis (ethylsulphonyl) derivatives of sugars is discussed in the light of these observations. © 1987.

Original languageEnglish
Pages (from-to)403-414
Number of pages12
JournalCarbohydrate Research
Volume164
Issue numberC
Publication statusPublished - 1 Jul 1987

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Methane
Derivatives
Methylation
Sugars
Methanol
Degradation
propylene
pyridine

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Grant Buchanan, J., Edgar, A. R., & Hutchison, R. J. (1987). Rearrangement of derivatives of bis(ethylsulphonyl)-α-d-lyxopyranosylmethane. Carbohydrate Research, 164(C), 403-414.
Grant Buchanan, J. ; Edgar, Alan R. ; Hutchison, Roderick J. / Rearrangement of derivatives of bis(ethylsulphonyl)-α-d-lyxopyranosylmethane. In: Carbohydrate Research. 1987 ; Vol. 164, No. C. pp. 403-414.
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Grant Buchanan, J, Edgar, AR & Hutchison, RJ 1987, 'Rearrangement of derivatives of bis(ethylsulphonyl)-α-d-lyxopyranosylmethane', Carbohydrate Research, vol. 164, no. C, pp. 403-414.

Rearrangement of derivatives of bis(ethylsulphonyl)-α-d-lyxopyranosylmethane. / Grant Buchanan, J.; Edgar, Alan R.; Hutchison, Roderick J.

In: Carbohydrate Research, Vol. 164, No. C, 01.07.1987, p. 403-414.

Research output: Contribution to journalArticle

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Grant Buchanan J, Edgar AR, Hutchison RJ. Rearrangement of derivatives of bis(ethylsulphonyl)-α-d-lyxopyranosylmethane. Carbohydrate Research. 1987 Jul 1;164(C):403-414.