81087-02-7

Upstream product

• 108-24-7 acetic anhydride 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 57-50-1 Sucrose 
• 34382-02-0 2,3,4,3',4'-penta-O-acetylsucrose 
• 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 

Downstream Products

• 309261-86-7 3,4,6-tri-O-acetyl-1-O-tert-butyldiphenylsilyl-β-D-fructofuranosyl-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside 

Relevant academic research and scientific papers

Facile conversion of O-silyl protected sugars into their corresponding formates using POCl3·DMF complex

The direct O-formylation of two selectively protected sugar derivatives using the Vilsmeier-Haack (V-H) complex POCl3·DMF was studied. Primary O-TBDMS and O-TBDPS ethers of sucrose, the most common disaccharide, underwent regio and chemoselecti

BRANCHED-CHAIN SUCROSES: SYNTHESIS AND WITTIG REACTION OF THE 1'-ALDEHYDO DERIVATIVE OF SUCROSE

The reaction of 2,3,4,3',4'-penta-O-acetylsucrose (1) with 3.3 mol. equv. of tert-butyldiphenylsilyl chloride in pyridine in the presence of 4-dimethylaminopyridine gave the 6,1',6'-tris(tert-butyldiphenylsilyl) derivative 2 (27percent) and the 6,6'-bis(t

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.