81087-01-6

Upstream product

• 58479-61-1 tert-butylchlorodiphenylsilane 
• 57-50-1 Sucrose 
• 98-88-4 benzoyl chloride 

Downstream Products

• 1055037-08-5 1-O-tert-butyldiphenylsilyl-3,4-di-O-benzoyl-β-D-fructofuranosyl-2,3,4-tri-O-benzoyl-α-D-glucopyranoside 
• 81086-97-7 (2R,3R,4S,5S)-2-[(2S,3S,4S,5R)-2,5-Bis-(tert-butyl-diphenyl-silanyloxymethyl)-3,4-dihydroxy-tetrahydro-furan-2-yloxy]-6-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-pyran-3,4,5-triol 

Relevant academic research and scientific papers

Chemical synthesis of 1′-deoxy-1′-fluorosucrose

The first chemical synthesis of 1′-deoxy-1′-fluorosucrose has been accomplished in eight steps from sucrose by an unlikely, but ultimately successful, SN2 displacement reaction.

SYNTHESIS AND REACTIONS OF tert-BUTYLDIPHENYLSILYL ETHERS OF SUCROSE

The reaction of sucrose with 1.1 mol. equiv. of tert-butyldiphenylsilyl (t-BDPS) chloride in pyridine in the presence of 4-dimethylaminopyridine gave the crystalline 6'-t-BDPS ether 1 in 49percent yield, without recourse to column chromatography.Compound 1 was transformed into the 4,6,1'-trichloride by using sulphuryl chloride.When the silylation reaction of sucrose was performed with 3 mol. equiv. of the reagent, chromatography gave the crystalline 6,6'-di-t-BDPS ether and the 6,1',6'-tri-t-BDPS ether 9 in yield of 78 and 18.7percent, respectively.Compound 9 was obtained as the major product on treatment of sucrose with 4.6 mol.equiv. of the silylating reagent.Removal of the silyl protecting-group in 6,6'-di-O-ter-butyldiphenylsilylsucrose hexabenzoate, using tetrabutylammonium fluoride, proceeded smoothly, but with 4->6 migration of the benzoate.