118895-89-9

Upstream product

• 108-24-7 acetic anhydride 
• 100-51-6 benzyl alcohol 
• 35781-78-3 5,6-anhydro-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose 
• 100-44-7 benzyl chloride 
• 53928-30-6 1,2-O-isopropylidene-3,5,6-tri-O-benzyl-α-D-glucofuranoside 
• 18549-40-1 1,2-O-isopropylidene-α-D-glucofuranose 
• 81823-12-3 1,2-O-isopropylidene-3,6-di-O-benzyl-α-D-glucofuranose 

Downstream Products

• 81823-12-3 1,2-O-isopropylidene-3,6-di-O-benzyl-α-D-glucofuranose 

Relevant academic research and scientific papers

Synthesis of peracetylated chacotriose

Steroidal glycoalkaloids of many Solanum species have recognized biological activities, especially those containing the glycosyl moiety α-L-rhamnopyranosyl-(1 → 2)-[α-L-rhamnopyranosyl-(1 → 4)]-D-glucopyranose (chacotriose) whose peracetate is here synthe

Syntheses and reactions of 5-O-acetyl-1,2-anhydro-3-O-benzyl-α-D-ribofuranose and -β-D-lyxofuranose, 5-O-acetyl-1,2-anhydro-3,6-di-O-benzyl- and 1,2-anhydro-5,6-di-O-benzoyl-3-O-benzyl-β-D-mannofuranose, and 6-O-acetyl-1,2-anhydro-3,4-di-O-benzyl-α-D-glucopyranose and -β-D-talopyranose

The title compounds 5-O-acetyl-1,2-anhydro-3-O-benzyl-α-D-ribofuranose and 5-O-acetyl-1,2-anhydro-3-O-benzyl-β-D-lyxofuranose, and 6-O-acetyl-1,2-anhydro-3,4-di-O-benzyl-α-D-glucopyranose and 6-O-acetyl-1,2-anhydro-3,4-di-O-benzyl-β-D-talopyranose, and 5-O-acetyl-1,2-anhydro-3,6-di-O-benzyl-β-D-mannofuranose and 1,2-anhydro-5,6-di-O-benzoyl-3-O-benzyl-β-D-mannofuranose have each been synthesized from the corresponding 2-O-tosylate and 1-free hydroxyl intermediates by base-initiated intramolecular SN2 ring closure in almost quantitative yields. Acetyl and benzoyl groups were not affected in the ring closure reactions. Condensation of 6-O-acetyl-1,2-anhydro-3,4-di-O-benzyl-α-D-glucopyranose and 5-O-acetyl-1,2-anhydro-3,6-di-O-benzyl-β-D-mannofuranose with 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose in the presence of ZnCl2 as the catalyst afforded the 1,2-trans-linked 6-O-acetyl-3,4-di-O-benzyl-β-D-glucopyranosyl-(1 → 6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose and 5-O-acetyl-3,6-di-O-benzyl-α-D-mannofuranosyl-(1 → 6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose as the sole products in satisfactory yields, while condensation of 5-O-acetyl-1,2-anhydro-3-O-benzyl-β-D-lyxofuranose with 3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose yielded the 1,2-trans-linked 5-O-acetyl-3-O-benzyl-α-D-lyxofuranosyl-(1 → 5)-3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose as the sole product in a good yield. The 6-O-acetyl group in the glycosyl donor, 6-O-acetyl-1,2-anhydro-3,4-di-O-benzyl-α-D-glucopyranose, did not influence the stereoselectivity of the ring-opening-coupling reaction.

Regioselective De-O-benzylation with Lewis Acids

Simple and highly regioselective de-O-benzylations of poly-O-benzylated monosaccharides and polyols with Lewis acids (SnCl4 and TiCl4) were developed.Spectral studies on intermediates complexes showed that three appropriately situated metal chelating functional groups were necessary for the selective de-O-benzylation.