TY - JOUR
T1 - Glycosidation of 3,4,6-tri-o-benzyl-2-ethenyl-D-glucal - A route to 2-C-(β-methyl)methylene glycosides
AU - Feit, Ben Ami
AU - Kelson, Idil Kasuto
AU - Gerull, Anke
AU - Abramson, Sarah
AU - Schmidt, Richard R.
PY - 2000
Y1 - 2000
N2 - Monosaccharidic and disaccharidic 2-C-(β-methyl)methylene glycosides were synthesized by an electrophilic conjugate addition reaction of ROH-type compounds in the presence of Ph3+PH Br- to 2-ethenyl-3,4,6-tri-O-benzyl-D-glucal 1, functioning as a model glycosyl donor. This 2-vinyl glucal derivative represents a series of 2-vinyl and 2-butadienyl glycals, prepared by Wittig-type methylenation of pyranosidic conjugated enals, derived from glucal, galactal and lactal. The exo-(β-methyl)methylene group paves the way for further chemical transformations.
AB - Monosaccharidic and disaccharidic 2-C-(β-methyl)methylene glycosides were synthesized by an electrophilic conjugate addition reaction of ROH-type compounds in the presence of Ph3+PH Br- to 2-ethenyl-3,4,6-tri-O-benzyl-D-glucal 1, functioning as a model glycosyl donor. This 2-vinyl glucal derivative represents a series of 2-vinyl and 2-butadienyl glycals, prepared by Wittig-type methylenation of pyranosidic conjugated enals, derived from glucal, galactal and lactal. The exo-(β-methyl)methylene group paves the way for further chemical transformations.
UR - http://www.scopus.com/inward/record.url?scp=0034407891&partnerID=8YFLogxK
U2 - 10.1080/07328300008544109
DO - 10.1080/07328300008544109
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AN - SCOPUS:0034407891
VL - 19
SP - 661
EP - 675
JO - Journal of Carbohydrate Chemistry
JF - Journal of Carbohydrate Chemistry
SN - 0732-8303
IS - 6
ER -