TY - JOUR
T1 - Rearrangement of derivatives of bis(ethylsulphonyl)-α-d-lyxopyranosylmethane
AU - Grant Buchanan, J.
AU - Edgar, Alan R.
AU - Hutchison, Roderick J.
PY - 1987/7/1
Y1 - 1987/7/1
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=45949118170&partnerID=8YFLogxK
M3 - Article
SN - 0008-6215
VL - 164
SP - 403
EP - 414
JO - Carbohydrate Research
JF - Carbohydrate Research
IS - C
ER -