154077-75-5

Upstream product

• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 37812-69-4 1-O-(2′-naphthyl)-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 6044-30-0 naphthyl-beta-D-glucopyranoside 

Downstream Products

• 872506-42-8 2-naphthyl 4,6-O-benzylidene-2,3-di-O-acetyl-β-D-glucopyranoside 

Relevant academic research and scientific papers

Enantioselective cyclopropanation of conjugated cyanosulfones using carbohydrate-based crown ether catalysts

A few new D-galactose- and D-glucose-based monoaza-15-crown-5 type lariat ethers have been synthesized. These macrocycles and their derivatives proved to be efficient catalysts in the cyclopropanation of (E)-3-phenyl-2-(phenylsulfonyl)acrylonitrile performed with diethyl bromomalonate under mild phase transfer conditions. Among the catalysts tested, the macrocycle having methyl α-D-galactopyranoside unit generated the highest asymmetric induction (80% ee). In the reactions of the aryl-substituted phenylsulfonyl-acrylonitrile derivatives, the cyclopropanation of the meta- and para-substituted starting materials took place with high ee values (75–84% ee). The cyclopropane derivatives synthesized from analogous α,β-unsaturated cyanosulfones containing naphthyl, pyridyl, furyl and thienyl groups were obtained with enantioselectivities up to 85%, and in excellent yields.

FeCl3 mediated arylidenation of carbohydrates

Glycosides and thioglycosides based on monosaccharides in reaction with benzaldehyde dimethylacetal or p-methoxybenzaldehyde dimethyl acetal undergo FeCl3-catalyzed (20 mol %) regioselective 4,6-O-arylidenation producing the corresponding acetals in high yields. FeCl3 also mediates acetalation of glycosides and thioglycosides of cellobiose, maltose, and lactose affording the corresponding 4′,6′-O-benzylidene acetals, which were isolated after their acetylation in situ with acetic anhydride and pyridine. The combined yields (two steps) of these final products are also high (61-84%). The procedure is applicable to a wide variety of functional groups including -OBn.

Mild and efficient direct aromatic iodination

Aryl iodides are important synthetic intermediates that can be transformed into tritium labelled compounds by metal-mediated hydrodehalogenation and also react in a number of important synthetic transformations. We present ICl/In(OTf)3 as a new reagent combination for mild iodination, suitable for acid-sensitive substrates such as carbohydrates.