120403-27-2Relevant articles and documents
Rapid Synthesis of l-Idosyl Glycosyl Donors from α-Thioglucosides for the Preparation of Heparin Disaccharides
Herczeg, Mihály,Demeter, Fruzsina,Balogh, Tímea,Kelemen, Viktor,Borbás, Anikó
supporting information, p. 3312 - 3316 (2018/07/13)
A new methodology for the synthesis of the most challenging heparin building block has been developed. Orthogonally protected l-idosyl glycosyl donors were prepared by C5 epimerization of the corresponding thioglucosides using the hydroboration/oxidation method followed by a 4,6-acetal formation. The α-anomeric configuration was crucial, and the bulky C4 substituent was advantageous for the high l-ido diastereoselectivity. The 4,6-arylmethylene group proved to be a directing element in glycosylation, whereby stereoselective α-idosylation could be achieved by using idosyl donors without a C-2 participating group.
Synthesis of cis-(1 → 3)-glycosides of allyl 2-acetamido-4,6-O- benzylidene-2-deoxy-α-D-glucopyranoside
Madaj, Janusz,Jankowska, Magdalena,Wisniewski, Andrzej
, p. 1293 - 1300 (2007/10/03)
Syntheses of allyl 2,3,4-tri-O-benzyl-α-D-gluco- and D-galactopyranosyluronate-(1→3)-2-acetamido-4,6-O-benzylidene-2-deoxy- α-D-glucopyranoside via oxidation of the hydroxymethyl group of allyl 2,3,4-tri-O-benzyl-α-D-gluco- and D-galactopyranosyl-(1→3)-2-
Use of the methylsulfenyl cation as an activator for glycosylation reactions with alkyl (aryl) 1-thioglycopyranosides: synthesis of methyl O-(2-acetamido-2- deoxy-beta-D-glucopyranosyl)-(1----6)-O-alpha-D-glucopyranosyl-(1----2) -alpha-D -glucopyranoside, a derivative of the core trisaccharide of E. coli K12.
Dasgupta,Garegg
, p. 225 - 238 (2007/10/02)
Methylsulfenyl bromide (MSB) and methylsulfenyl trifluoromethanesulfonate (MST) have been used to prepare 1,2-cis-linked disaccharides. Ethyl (phenyl) 1-thio-beta-D-gluco- and galacto-pyranosides having non-participating (benzyloxy) protecting groups were used as the donors. The alpha beta-ratio of the products depended on the promoter and conditions of reaction. Intimate ion-pairs, formed initially, may be responsible for the steric outcome of the glycosylations. Thus, with ethyl 2,3,4,6-tetra-O-benzyl-alpha-D-mannopyranoside as a donor, moderate quantities of the beta-linked disaccharide could be produced using MSB as the activator. The synthesis of the title trisaccharide glycoside that contains 1,2-cis and 1,2-trans-linkages is described.