110920-92-8

Upstream product

• 58479-61-1 tert-butylchlorodiphenylsilane 
• 18549-40-1 1,2-O-isopropylidene-α-D-glucofuranose 
• 110920-93-9 3,5-O-benzylidene-6-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-α-D-glucofuranose 

Downstream Products

• 110920-93-9 3,5-O-(R)-benzylidene-6-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-α-D-glucofuranose 
• 140451-84-9 5-Azido-3-O-benzoyl-5-deoxy-1,2-O-isopropylidene-6-O-tert-butyldiphenylsilyl-α-D-allofuranose 
• 140451-85-0 5-azido-3-O-benzoyl-6-O-tert-butyldiphenylsilyl-5-deoxy-1,2-O-isopropylidene-α-D-glucofuranose 
• 140451-82-7 3-O-benzoyl-5-bromo-6-O-tert-butyldiphenylsilyl-5-deoxy-1,2-O-isopropylidene-α-D-allofuranose 
• 141242-28-6 5-bromo-6-O-tert-butyldiphenylsilyl-5-deoxy-1,2-O-isopropylidene-β-L-talofuranose 
• 141242-33-3 3-O-benzoyl-6-O-tert-butyldiphenylsilyl-5-deoxy-1,2-O-isopropylidene-β-L-threo-hex-4-enofuranose 
• 141242-29-7 5-azido-6-O-tert-butyldiphenylsilyl-5-deoxy-1,2-O-isopropylidene-α-D-allofuranose 
• 141242-35-5 5-azido-6-O-tert-butyldiphenylsilyl-3,5-dideoxy-3-fluoro-1,2-O-isopropylidene-α-D-glucofuranose 
• 108782-72-5 3,6-di-O-benzoyl-5-bromo-5-deoxy-1,2-O-isopropylidene-β-L-idofuranose 
• 141242-34-4 3,6-di-O-benzoyl-5-deoxy-1,2-O-isopropylidene-β-L-threo-hex-4-enofuranose 
• 141242-37-7 5-Azido-6-O-benzoyl-1,3,5-dideoxy-3-fluoro-1,2-O-isopropylidene-α-D-glucofuranose 
• 141242-30-0 3-O-benzoyl-5-bromo-5-deoxy-1,2-O-isopropylidene-β-L-idofuranose 
• 111003-74-8 3,5-O-(R)-benzylidene-6-deoxy-6-iodo-1,2-O-isopropylidene-α-D-glucofuranose 
• 108865-15-2 3,5-O-(R)-benzylidene-1,2-O-isopropylidene-α-D-glucofuranose 

Relevant academic research and scientific papers

Truly catalytic and chemoselective cleavage of benzylidene acetal with phosphomolybdic acid supported on silica gel

Phosphomolybdic acid supported on silica gel provides a truly catalytic method for the chemoselective cleavage of benzylidene acetals having sensitive functional groups under mild conditions. It is easy to perform on large scale owing to minimal catalyst loading (0.5 mol-%). Several sensitive functional groups such as TBDPS ether, -OMs, -OAc, allyl ether, N-Boc, N-Fmoc and N-Cbz are stable under the reaction conditions. In addition, benzylidene acetal is selectively cleaved in the presence of isopropylidene ketal. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Synthesis of tetrahydropyrans from sugar lactones

Dehydration of both γ- and δ- hexonolactones, either by intramolecular nucleophilic displacement of triflate leaving groups at C-2, or by Mitsunobu type displacement of the OH-6, provides access to bicyclic lactones which contain tetrahydropyran rings. Reduction or nucleophilic ring opening of these bicyclic lactones furnishes polyfunctionalised tetrahydropyrans in good yield.

Synthesis, reactions, and crystal structure of 5-azido-6-O-benzoyl-3,5-dideoxy-3-fluoro-1,2-O-isopropylidene-α-D-gluc ofuranose

5-Bromo-6-O-tert-butyldiphenylsilyl-5-deoxy-1,2-O-isopropylidene-β-L-t alofuranose (7) was obtained by treatment of 3,5-O-benzylidene-6-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-α-D -glucofuranose (3) with N-bromosuccinimide followed by Zemplen O-dea

SPECIFIC SYNTHESIS AND STEREOCHEMICAL ASSIGNMENT OF THE DIASTEREOMERIC 3,5-O-BENZYLIDENE-1,2-O-ISOPROPYLIDENE-α-D-GLUCOFURANOSE ISOMERS

Pyridinium tosylate-catalysed acetal exchange between benzaldehyde dimethyl acetal and 6-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-α-D-glucofuranose was investigated as an alternative to the original procedure of Brigl and Gruener (condensation of