66657-12-3

Upstream product

• 50256-94-5 Benzyl-2,4-di-O-p-tosyl-α-D-xylopyranosid 
• 65359-87-7 benzyl 2,3-anhydro-β-L-ribopyranoside 
• 71204-45-0 benzyl 2,3-anhydro-4-O-trifluoromethanesulfonyl-β-L-ribopyranoside 

Downstream Products

• 80354-03-6 Benzyl-3,4-diazido-3,4-didesoxy-α-D-arabinopyranosid 
• 78907-34-3 benzyl-2,3-anhydro-4-amino-4-desoxy-α-D-lyxopyranoside 

Relevant academic research and scientific papers

Efficient Synthesis of 4-Substituted 2,3-Anhydro Sugars from 2,4-Di-O-tosylates

Treatment of benzyl 2,4-di-O-p-tosyl-α-D-xylopyranoside (1) with sodium methoxide/methanol yields benzyl 3,4-anhydro-2-O-p-tosyl-β-L-arabinopyranoside (2) and benzyl 2,3-anhydro-4-O-p-tosyl-α-D-lyxopyranoside (3) in a ratio of 50 : 1.Reaction of 2 with sodium methoxide leads to benzyl 2,3-anhydro-4-O-methyl-α-D-lyxopyranoside (4) and with sodium azide to benzyl 2,3-anhydro-4-azido-4-deoxy-α-D-lyxopyranoside (5).In the latter synthesis small amounts of benzyl 3,4-diazido-3,4-dideoxy-α-D-arabinopyranoside (7) are formed as a side product.

C-4-Triflate Displacement by Azide in 2,3-Anhydro Sugars; a New Way to 4-Amino-4-deoxy Sugars

Displacement of the triflyl by the azido group in benzyl-2,3-anhydro-4-triflyl-α-D-pyranosides 4-6 gives with inversion the benzyl-2,3-anhydro-4-azido-4-deoxypyranosides 7-9.The triflyl group turns out to be a reactive leaving group which can be replaced