13121-49-8

Upstream product

• 78890-68-3 1-deoxy-2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 176300-26-8 1-deoxy-2,3-di-O-benzyl-4,6-O-benzylidene-D-glucopyranose 
• 100-39-0 benzyl bromide 
• 65391-44-8 1,5-anhydro-4,6-O-(R)-benzylidene-D-glucitol 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 13137-69-4 1-deoxy-D-glucose tetraacetate 
• 177553-27-4 (2R,3R,4R,5S)-3,4,5-Tris-benzyloxy-2-trityloxymethyl-tetrahydro-pyran 
• 135560-99-5 Dimethyl-phenylethynyl-((2R,3R,4S,5R)-3,4,5-tris-benzyloxy-6-phenylselanyl-tetrahydro-pyran-2-ylmethoxy)-silane 
• 604-69-3 β-D-glucose pentaacetate 
• 154-58-5 1,5-anhydro-D-glucitol 

Downstream Products

• 912848-00-1 2-((2,3,4-tri-O-benzyl-β-D-xylopyranosyl)methyl)naphthalene 
• 912847-96-2 2,6-anhydro-3,4,5-tri-O-benzyl-L-glucose 

Relevant academic research and scientific papers

Synthesis and comparative structure-activity study of carbohydrate-based phenolic compounds as α-glucosidase inhibitors and antioxidants

Twenty-one natural and unnatural phenolic compounds containing a carbohydrate moiety were synthesized and their structure-activity relationship (SAR) was evaluated for α-glucosidase inhibition and antioxidative activity. Varying the position of the galloyl unit on the 1,5-anhydro -D-glucitol (1,5-AG) core resulted in changes in the α-glucosidase inhibitory activity and notably, particularly strong activity was demonstrated when the galloyl unit was present at the C-2 position. Furthermore, increasing the number of the galloyl units significantly affected the α-glucosidase inhibition, and 2,3,4,6-tetra-galloyl-1,5-AG (54) and 2,3,4,6-tetra-galloyl-d-glucopyranose (61) exhibited excellent activities, which were more than 13-fold higher than the α-glucosidase inhibitory activity of acertannin (37). Moreover, a comparative structure-activity study suggested that a hemiacetal hydroxyl functionality in the carbohydrate core and a biaryl bond of the 4,6-O-hexahydroxydiphenoyl (HHDP) group, which are components of ellagitannins including tellimagrandin I, are not necessary for the α-glucosidase inhibitory activity. Lastly, the antioxidant activity increased proportionally with the number of galloyl units.

Synthesis of aromatic C-xylosides by position inversion of glucose

Two formally C-xylosylated analogs to 2-naphthyl β-d-xylopyranoside, which is known to initiate priming of glucosaminoglycan chains, were synthesized by a position inversion of glucose (i.e., position 1 becomes position 5). The d-C-xyloside showed priming, while the l-C-xyloside did not initiate priming.

Triisobutylaluminium and dusobutylaluminium hydride as molecular scalpels: The regioselective stripping of perbenzylated sugars and cyclodextrins

To explain the remarkable regioselective de-O-benzylating properties of diisobutylaluminium hydride (DIBAL-H) and triisobutylaluminium (TIBAL) towards polybenzylated sugars or cyclodextrins, we propose a plausible mechanistic rationale critically involving the kinetic formation of a product-generating 2:1 Al-benzylated sugar complex. For the reaction to occur, one pair of adjacent oxygen atoms should first be able to form a chelation complex with the first equivalent of aluminium reagent, either a highly fluxional complex with tetracoordinate aluminium species or a pentacoordinate one. The second equivalent then induces the regioselectivity of the de-O-alkylation by coordinating preferentially to one of the oxygen atoms of the selected pair.

A new strategy for the stereoselective syntheses of C-glycosyl compounds of β-pentapyranoses

The C-glycosyl compounds of β-L-xylopyranose and β-D-arabinopyranose were conveniently prepared by reduction of methyl α-D-glucopyranoside and methyl α-D-mannopyranoside with triethylsilane in the presence of trimethylsilyl trifluoromethanesulfonate, respectively.