39698-00-5Relevant articles and documents
First Total Synthesis of Trehalose-Containing Branched Oligosaccharide OSE-1 of Mycobacterium gordonae (Strain 990)
Chaube, Manishkumar A.,Kulkarni, Suvarn S.
, p. 13544 - 13548 (2015)
The first total synthesis of the branched oligosaccharide OSE-1 of Mycobacterium gordonae (strain 990) is reported. An intramolecular aglycon delivery approach was used for constructing the desymmetrized 1,1′-α,α-linked trehalose moiety. A [3+2] glycosylation of the trisaccharide donor and trehalose acceptor furnished the right hand side pentasaccharide. Regioselective O3 glycosylation of L-rhamnosyl 2,3-diol allowed expedient synthesis of the left hand side tetrasaccharide. The nonasaccharide was assembled in a highly convergent fashion through a [4+5] glycosylation. Take the strain: First total synthesis of the branched oligosaccharide OSE-1 of Mycobacterium gordonae (strain 990) is reported. An intramolecular aglycon delivery approach was used for constructing the desymmetrized 1,1′-α,α-linked trehalose moiety. Regioselective O3 glycosylation of L-rhamnosyl 2,3-diol allowed expedient synthesis of the left hand side tetrasaccharide. The nonasaccharide was assembled in a highly convergent fashion through a [4+5] glycosylation.
Carbohydrate-based scaffolds for the generation of sortiments of bioactive compounds
Peri, Francesco,Cipolla, Laura,Forni, Eleonora,Nicotra, Francesco
, p. 369 - 382 (2007/10/03)
The polyfunctionality and conformational rigidity of carbohydrates make this class of compounds ideal scaffolds for the production of sortiments1 of bioactive compounds. Examples of carbohydrate-derived peptidomimetics of biological interest, such as somatostatin agonists and integrin antagonists, are presented. In order to have access to solid phase supported sortiments of compounds, orthogonally protected or unprotected carbohydrates were linked to polymers and reacted in the solid phase employing different regioselective strategies. Original bicyclic and tricyclic glycidic scaffolds were easily obtained starting from natural sugars such as D-arabinose and D-fructose. Manipulation of these conformationally blocked compounds afforded different carbohydrate-based derivatives, among which azidoacids are useful precursors of β-turn peptidomimetics.
Dehydrative Glycosylation Using Heptabenzyl Derivatives of Glucobioses and Lactose
Koto, Shinkiti,Morishima, Naohiko,Shichi, Sonoko,Haigoh, Hisamitsu,Hirooka, Motoko,et al.
, p. 3257 - 3274 (2007/10/02)
Dehydrative glycosylations of the 2-, 3-, 4-, and 6-OH groups of D-glucopyranose with hepta-O-benzyl derivatives of glucobioses (O-D-glucopyranosyl-(1->n)-D-glucopyranose; n = 2, 3, 4, or 6) and lactose, in the presence of a ternary mixture of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and triethylamine in dichloromethane showed that the selectivity of the reaction depended on the anomeric configuration and the linking position to the reducing tribenzylglucose moiety of the nonreducing tetrabenzylglucosyl residue and on the class of the OH group to be glycosylated.The use of a quaternary mixture of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, N,N-dimethylacetamide, and triethylamine made all but the β(1->2)-linked biosyl donor undergo α-condensation.Several new linear trisaccharides were obtained via debenzylation of the condensates.
