Synthesis of an appropriately protected core glycotetraoside, a key intermediate for the synthesis of "bisected" complex-type glycans of a glycoprotein.
A stereocontrolled synthetic route to a glycotetraoside, allyl O-(3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl)-(1--- -4)-O- (3,6-di-O-allyl-2-O-benzyl-beta-D-mannopyranosyl)-(1----4)-O-3, 6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl)-(1----4)-3-O- benzyl- 2-deoxy-6-O-p-methoxy-phenyl-2-phthalimido-beta-D-glucopyranoside, an important intermediate for the synthesis of "bisected" complex type glycans of glycoproteins has been established by employing two glycosyl donors, 3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl trichloroacetimidate and 4-O-acetyl-3,6-di-O-allyl-2-O-benzyl-alpha-D-mannopyranosyl bromide, and a glycosyl acceptor, allyl O-(3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl)-(1----4) -3-O- benzyl-2-deoxy-6-O-p-methoxyphenyl-2-phthalimido-beta-D-glucopyranoside.
Yamazaki
F
F
Riken (The Institute of Physical and Chemical Research), Saitama, Japan.
Kitajima
T
T
Nukada
T
T
Ito
Y
Y
Ogawa
T
T
D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D006027:Glycosides / Q000138:chemical synthesis*; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis*; D011134:Polysaccharides / Q000096:biosynthesis*
D006027:Glycosides; D009844:Oligosaccharides; D011134:Polysaccharides; C065739:allyl O-(3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-beta-Glup)(1-4)-O-(3,6-di-O-allyl-2-O-benzyl-beta-Manp)(1-4)-O-3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-Glup(1-4)-3-O-benzyl-2-deoxy-6-O-4-methoxyphenyl-2-phthalimido-beta-Glup