97292-02-9

Upstream product

• 100-39-0 benzyl bromide 
• 20888-02-2 1,6-anhydro-2,3,4-tri-O-benzyl-β-D-mannopyranose 
• 66963-52-8 (1R,2R,3S,4S,5R)-2,3-Bis-benzyloxy-4-[((E)-propenyl)oxy]-6,8-dioxa-bicyclo[3.2.1]octane 
• 66963-51-7 (1R,2R,3S,4S,5R)-4-Allyloxy-2,3-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]octane 
• 119005-81-1 1,6-anhydro-2-O-allyl-β-D-mannopyranose 
• 97292-00-7 1,6-Anhydro-2-O-(p-toluenesulphonyl)-β-D-mannopyranose 
• 97292-01-8 1,6-Anhydro-3,4-di-O-benzyl-2-O-(p-toluenesulphonyl)-β-D-mannopyranose 
• 157660-36-1 1,6-anhydro-4-O-benzyl-2,3-O-endo-benzylidene-β-D-mannopyranose 
• 71049-45-1 1,6-anhydro-2,3-O-endo-benzylidene-β-D-mannopyranose 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 67227-89-8 1,6-anhydro-3,4-di-O-benzyl-β-D-mannopyranoside 
• 14168-65-1 mannosan 

Downstream Products

• 55682-57-0 1,6-anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose 
• 86783-82-6 2-fluoro-D-glucose 
• 97292-03-0 1,6-Anhydro-3,4-di-O-benzyl-2-deoxy-2-fluoro-β-D-glucopyranose 
• 55682-48-9 1,6-anhydro-2-azido-3,4-di-O-benzyl-2-deoxy-D-glucopyranose 

Relevant academic research and scientific papers

Stereoselective synthesis of α-glycosyl azides by TMSOTf-mediated ring opening of 1,6-anhydro sugars

Access to α-glycosyl azides in modest to high diastereoselectivity by way of TMSN3 ring-opening of 1,6-anhydro sugars mediated by TMSOTf is reported. The reaction tolerates a wide variety of functional groups including alcohol, alkyne, azide and ester groups. The efficient synthesis of a pseudopentasaccharide in five steps from commercially available levoglucosan by way of a "click-click" approach is presented to highlight the interest of the TMSN3 ring-opening reaction. A new route to α-glycosyl azides by way of TMSN3 ring-opening of 1,6-anhydro sugars is presented. The potential of this methodology is demonstrated by the expeditious synthesis of a pseudopentasaccharide following a "click-click" approach.

Synthesis of a (1->6)-β-Linked N-Acetyl-D-glucosamine Oligosaccharide

1,6-Anhydro-2-deoxy-3,4-di-O-benzyl-2-phthalimido-β-D-glucopyranose (5) was synthesized from 1,6-anhydro-β-D-mannopyranose (1) in five steps.Compound 5 was polymerized under cationic conditions and selectively yielded glucosamine oligomers (degree of poly

Facile Preparation of 1,6-Anhydro-2-azido-3-O-benzyl-2-deoxy-β-D-glucopyranose and Its 4-O-Substituted Derivatives

Treatment of 1,6-anhydro-2,3-O-endo-benzylidene-β-D-mannopyranose derivatives with trimethylamine-borane (1/1)-aluminium chloride resulted in highly regioselective fission of the cyclic acetals to give the corresponding 2-O-unprotected-3-O-benzyl derivatives. Trifluoromethane-sulfonylation of these, followed by nucleophilic substitution, afforded 2-azido-2-deoxy derivatives in good yields.

Regioselective De-O-benzylation with Lewis Acids

Simple and highly regioselective de-O-benzylations of poly-O-benzylated monosaccharides and polyols with Lewis acids (SnCl4 and TiCl4) were developed.Spectral studies on intermediates complexes showed that three appropriately situated metal chelating functional groups were necessary for the selective de-O-benzylation.

Facile Preparation of 3,4-Di-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose and Some Derivatives Thereof: Useful Precursors for Oligosaccharide Synthesis

A facile, virtually one-pot synthesis of the title compound and also some of its derivatives is based on regioselective 2-substitutions of 1,6-anhydro-β-D-mannopyranose using stannylidene activation.The compounds thus prepared are useful precursors in the synthesis of glycoprotein-type oligosaccharides.

A New, High Yield Synthesis of 2-Deoxy-2-fluoro-D-glucose

The reaction of 1,6-anhydro-3,4-di-O-benzyl-2-O-(trifluoromethanesulphonyl)-β-D-mannopyranose (4) with tetraalkylammonium fluorides provides a rapid, high yield synthetic route to 2-deoxy-2-fluoro-D-glucose.