2-(2,3,4,6-Tetra-O-acetyl-b-D-glucopyranosyl)thiopseudourea hydrobromide - CAS 40591-65-9
Category:
Carbohydrates
Product Name:
2-(2,3,4,6-Tetra-O-acetyl-b-D-glucopyranosyl)thiopseudourea hydrobromide
CAS Number:
40591-65-9
Molecular Weight:
487.32
Molecular Formula:
C15H23BrN2O9S
COA:
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MSDS:
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Structure:
Monosaccharides
Chemical Structure
CAS 40591-65-9 2-(2,3,4,6-Tetra-O-acetyl-b-D-glucopyranosyl)thiopseudourea hydrobromide

Related Monosaccharides Products


Reference Reading


1.Synthesis of fluorescent and radioactive analogues of two lactosylceramides and glucosylceramide containing beta-thioglycosidic bonds that are resistant to enzymatic degradation.
Albrecht B1, Pütz U, Schwarzmann G. Carbohydr Res. 1995 Oct 23;276(2):289-308.
Condensation of 2-S-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-2- thiopseudourea hydrobromide with 2,3,6-tri-O-benzoyl-4-O-trifluoromethylsulfonyl-beta-D-galactopyra nosyl- (1-->1)-(2S,3R,4E)-3-O-benzoyl-2-dichloroacetamido-4-octa decen-1,3-diol afforded S-(2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl)-(1-->4)-2,3,6-tri-O- benzoyl-4-thio-beta-D-glucopyranosyl-(1-->1)-(2S,3R,4E)-3-O-benzoy l-2- dichloroacetamido-4-octadecen-1,3-diol in good yield. Removal of the protecting groups, followed by selective N-acylation of the sphingosine amino group with either a fluorescent or a radioactive fatty acid, gave labeled lactosylceramide analogues in good yield. Since these products contained a beta-thioglycosidic bond between the two sugar moieties, they were totally resistant to the action of acid lysosomal glycosidases. Likewise, condensation of 2-S-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)-2- thiopseudourea hydrobromide and 2,3,4,6-tetra-O-acetyl-beta-D-galactopyranosyl-(1-->4)-2,3,6- tri-O-acetyl-1-S-acetyl-1-thio-beta-D-glucopyranose with (2R,3R,4E)-3-O-benzoyl-2-dichloroacetamido-1-iodo-4-octad ecen-3-ol in methanolic sodium acetate afforded the corresponding beta-thioglycosides 14 and 16, respectively, in good yield.