91513-13-2Relevant academic research and scientific papers
Efficient Synthesis of 4-Substituted 2,3-Anhydro Sugars from 2,4-Di-O-tosylates
Kowollik, Wolfgang,Voelter, Wolfgang
, p. 433 - 436 (2007/10/02)
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.
