81348-19-8

Upstream product

• 3396-99-4 methyl α-D-galactopyranoside 
• 100-39-0 benzyl bromide 
• 108-24-7 acetic anhydride 
• 40010-11-5 methyl α-D-galactopyranoside 3-benzyl ether 
• 67-56-1 methanol 
• 314038-30-7 Acetic acid (2S,3R,4S,5R,6R)-5-acetoxy-6-acetoxymethyl-4-benzyloxy-2-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-3-yl ester 
• 18685-18-2 3-O-benzyl-1,2-5,6-O-diisopropylidene-α-D-glucofuranose 
• 39686-94-7 1,2,4,6-tetra-O-acetyl-3-O-benzyl-β-D-glucopyranose 
• 129706-93-0 methyl 3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 

Downstream Products

• 40010-11-5 methyl β-D-glucopyranoside 3-benzyl ether 
• 1372631-55-4 methyl 3-O-benzyl-2,4-di-O-(trifluoromethanesulfonyl)-6-O-trityl-β-D-glucopyranoside 
• 1372631-67-8 N-benzyl-3-O-benzyl-2,4-dideoxy-2,4-imino-D-talitol 
• 566197-59-9 methyl 3-O-benzyl-6-O-tosyl-β-D-glucopyranoside 
• 566197-67-9 methyl 2,4-di-O-acetyl-3-O-benzyl-6-deoxy-6-acetylamino-β-D-glucopyranoside 

Relevant academic research and scientific papers

Visible-Light-Mediated Oxidative Debenzylation Enables the Use of Benzyl Ethers as Temporary Protecting Groups

The cleavage of benzyl ethers by catalytic hydrogenolysis or Birch reduction suffers from poor functional group compatibility and limits their use as a protecting group. The visible-light-mediated debenzylation disclosed here renders benzyl ethers temporary protective groups, enabling new orthogonal protection strategies. Using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as a stoichiometric or catalytic photooxidant, benzyl ethers can be cleaved in the presence of azides, alkenes, and alkynes. The reaction time can be reduced from hours to minutes in continuous flow.

Azetidine iminosugars from the cyclization of 3,5-Di- O -triflates of α-furanosides and of 2,4-Di- O -triflates of β-pyranosides derived from glucose

Primary amines with either 3,5-di-O-ditriflates of α-furanosides or 2,4-di-O-triflates of β-pyranosides form bicyclic azetidines in high yield.

Synthesis of novel HIV-1 protease inhibitors based on carbohydrate scaffolds

The synthesis of peptidomimetic inhibitors of HIV-1 protease based on 6-deoxy-6-amino-β-D-glucopyranoside and 6-deoxy-6-amino-β-D-mannopyranoside scaffolds has been achieved. The inhibitors had IC50 values in the micromolar range. The results provide a platform for the development of more potent carbohydrate based inhibitors of HIV-1 and other aspartic proteases.

REGIOSELECTIVE FORMATION OF DI-O-BENZYL-SUBSTITUTED HEXOPYRANOSIDES VIA STANNYLENE ACETAL INTERMEDIATES

The reactions of dibutylstannylene acetals derived from several methyl hexopyranosides with benzyl bromide have been investigated.These reactions occur readily in benzyl bromide at 85 deg C.At reaction times of one to two days, the major products are di-O-benzyl derivatives.In several cases, single di-O-benzyl derivatives are the predominant products: methyl α-D-glucopyranoside and methyl β-D-galactopyranoside gave the 2,6- and 3,6-di-O-benzyl ethers in 82 and 70percent yields, respectively.The species present in these reactions and the reaction pathway are discussed.