13242-48-3Relevant articles and documents
Pathways in the synthesis of functionalized glycolipids for liposomal preparations
Ionescu, C?t?lina,Huseynova, Fidan,Barragan-Montero, Véronique
, (2021/12/01)
We describe in this paper the synthesis of two glycolipids containing a mannosyl residue functionalized with malonic acid and azide groups at the C6 position. Two synthetic routes have been successfully implemented: the first one involves Schmidt's glycosylation procedure using functionalized carbohydrates, whereas the second one involves nucleophilic substitutions in the C6 position of an iodinated intermediate obtained using Koenigs-Knorr reaction. A comparative discussion of reactions and yields is realized. The two glycolipids served as material for the preparation of liposomes.
A practical large-scale access to 1,6-anhydro-β-D-hexopyranoses by a solid-supported solvent-free microwave-assisted procedure
Bailliez, Vincent,De Figueiredo, Renata M.,Olesker, Alain,Cleophax, Jeannine
, p. 1015 - 1017 (2007/10/03)
Microwave irradiation of 6-O-tosyl or 2,6-di-O-tosyl peracetylated hexopyranoses absorbed on basic alumina in a dry medium afforded the corresponding 1,6-anhydro-β-D-hexopyranoses. A direct access to 1,6:3,4-dianhydro-β-D-altropyranose (16) from D-glucose is also described.
Studies related to synthesis of glycophosphatidylinositol membrane-bound protein anchors. 6. Convergent assembly of subunits
Madsen, Robert,Udodong, Uko E.,Roberts, Carmichad,Mootoo, David R.,Konradsson, Peter,Fraser-Reid, Bert
, p. 1554 - 1565 (2007/10/02)
Glycophosphatidylinositol anchors of membrane-bound proteins are thought to comprise a common pentasaccharide core containing mannan, glucosamine, and inositol residues. A synthetic route to this core is described. In addition, the complete heptasaccharide moiety of the rat brain Thy-1 membrane anchor, the first mammalian membrane anchor to be characterized, has been synthesized. In the case of the Thy-1 anchor, the synthetic plan is based on three building blocks comprising glucosamine-inositol, galactosamine-mannose, and trimannan residues. Although glycosyl donors other than n-pentenyl glycosides (NPGs) have been used in preparing each of these building blocks, the final assembly of the heptasaccharide utilizes NPGs as the only glycosyl donors. The mildness of the conditions for these coupling reactions has allowed us to make provisions for subsequent installation of the three phosphodiester units.
Radical oxygenation of 2-Dexyy-2-iodo hexopyranosides with molecular oxygen
Moutel,Prandi
, p. 8163 - 8166 (2007/10/02)
2-Deoxy-2-iodo hexopyranosides react with molecular oxygen and tributylstannane to give the epimeric C-2 alcohols in high yield and moderate selectivity.
2,3,4-Tri-O-acetyl-1,6-anhydro-β-D-mannopyranose, an artifact produced during carbohydrate analysis. A total synthesis of 2,3,5-tri-O-acetyl-1,6-anhydro-β-D-mannofuranose
Manna,McAnalley,Ammon
, p. 11 - 27 (2007/10/02)
This study confirms that 2,3,4-tri-O-acetyl-1,6-anhydro-β-D-mannopyranose is an artifact produced during carbohydrate analysis. A new synthesis of 2,3,5-tri-O-acetyl-1,6-anhydro-β-D-mannofuranose is also described, and a novel dimer, 1,6':6,1'-dianhydro-2,3:2',3'-di-O-isopropylidene-5,5'-di-O-(1-methoxy ethyl)-di-α-D-mannofuranose, has been isolated. The structure of the dimer is confirmed by X-ray analysis of a derivative, 1,6':6,1'-dianhydro-2,3:2',3'-di-O-isopropylidene-di-α-D-mannofuranos e. This study confirms that 2,3,4-tri-O-acetyl-1,6-anhydro-β-D-mannopyranose is an artifact produced during carbohydrate analysis. A new synthesis of 2,3,5-tri-O-acetyl-1,6-anhydro-β-D-mannofuranose is also described, and a novel dimer, 1,6′:6,1′- dianhydro-2,3:2′,3′-di-O- isopropylidene-5,5′-di-O-(1-methoxyethyl)-di-α-D- mannofuranose, has been isolated. The structural of the dimer is confirmed by X-ray analysis of a derivative, 1,6′:6, 1′-dianhydro-2,3:2′,3′-di-O-isopropylidene- di-α-D-mannofuranose.
A Mild Procedure for Cleavage of 1,6-Anhydro Sugars
Zottola, Mark,Rao, B. Venkateswara,Fraser-Reid, Bert
, p. 969 - 970 (2007/10/02)
Acetolysis of 1,6-anhydro sugars can be achieved by treatment with acetic anhydride and triethylsilyl trifluoromethanesulphonate at 0 deg C for 5-15 minutes, under which conditions a wide variety of protecting groups are unaffected, and even the trisulphonate is cleaved, albeit in six hours.
A Mild Procedure for the Preparation of 1,6-Anhydro-β-D-hexopyranoses and Derivatives
Lafont, Dominique,Boullanger, Paul,Cadas, Olivier,Descotes, Gerard
, p. 191 - 194 (2007/10/02)
Treatment of reducing 6-O-tosyl-D-glucopyranoses 1 with 1,8-diazabicycloundec-7-ene (DBU) afforded the corresponding 1,6-anhydro-β-D-hexopyranoses 2 in high yields.Reaction was also performed on partly acetylated tosylates of carbohydrates.
1,6-Anhydrofuranoses, XI. - 1,6-Anhydro-α-L-idofuranose
Koell, Peter,John, Hans-Georg,Schulz, Juergen
, p. 613 - 625 (2007/10/02)
The title compound 13 is prepared on different routes from suitable benzyl derivatives with gluco-configuration.Preparations use the susceptibility of axial 5-O-benzyl groups in this compounds to selective hydrogenolysis, thus allowing subsequent inversion of configuration in this position from D-gluco to L-ido by an oxidation/reduction sequence.Only 0.08percent of 13 are found in the equilibrium mixture of idose in acidic medium.It is shown with 4-C-methyltalose as example, that the amount of 1,6-anhydrofuranoses in these equilibria rises significantly by changing the hydroxy groups in 4-position from secondary to tertiary ones.
