Pivalates in the selective protection and activation of maltose for the synthesis of sulfated 3-deoxy-maltosyl-(1-->4)-alpha, alpha-trehalose.
Pivaloylation of maltose gave, in satisfactory yield, 1,2,6,2',3',4',6'-hepta-O-pivaloyl-beta-maltose which was converted to the 3-deoxygenated analogue in a Barton-McCombie reaction. This compound was used directly in a trimethylsilyl triflate-mediated glycosylation reaction with 2,3,6-tri-O-benzyl-alpha-D-glucopyranosyl 2,3-di-O-benzyl-4,6-O-benzylidene-alpha-D-glucopyranoside to give the corresponding maltosyl-(1-->4)-alpha, alpha-trehalose derivative. After deprotection, the monodeoxygenated tetrasaccharide was sulfated; in the reaction product, one compound fully sulfated at the outer pyranose rings predominated.
Wessel
H P
HP
F. Hoffmann-La Roche Ltd., Pharma Division, Basel, Switzerland.
Trumtel
M
M
D002240:Carbohydrate Sequence; D009682:Magnetic Resonance Spectroscopy; D008320:Maltose / Q000737:chemistry*; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D013431:Sulfates / Q000138:chemical synthesis; D014199:Trehalose / Q000031:analogs & derivatives* / Q000737:chemistry
C105301:3-deoxymaltosyl-1-4-alpha,alpha-trehalose; D009844:Oligosaccharides; D013431:Sulfates; D008320:Maltose; D014199:Trehalose