104292-76-4

Upstream product

• 104292-68-4 Benzyl 2,3-anhydro-4-deuterio-α-D-lyxopyranoside 
• 104292-65-1 benzyl 3,4-anhydro-β-L-ribopyranoside 
• 104292-63-9 benzyl 4-bromo-4-deoxy-α-D-lyxopyranoside 
• 104292-69-5 benzyl 3,4-anhydro-β-L-erythropentopyranosid-2-ulose 
• 104292-73-1 benzyl 2-deuterio-3,4-O-isopropylidene-β-L-arabinopyranoside 
• 18403-22-0 (3aS,6S,7R,7aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol 
• 104292-74-2 C₂₂H₂₅⁽²⁾HO₇S 
• 104322-44-3 C₁₉H₂₁⁽²⁾HO₇S 
• 65247-32-7 benzyl 3,4-O-(1-methylethylidene)-β-L-erythro-pent-2-ulosylpyranoside 
• 104322-43-2 benzyl 3,4-anhydro-2-deuterio-β-L-ribopyranoside 
• 104292-75-3 benzyl 2,3-anhydro-2-deuterio-β-L-ribopyranoside 
• 67412-71-9 (-)-benzyl 2,3-anhydro-β-D-ribopyranoside 
• 128843-83-4 Benzyl 2,3-anhydro-α-L-lyxopyranoside 

Relevant academic research and scientific papers

Chiral Aldehydes by Ring Contraction of Pento- and Hexopyranoside Epoxides

The chiral aldehydes (-)-(2S,5S)- and (-)-(2S,5R)-2-oxy>methyl>-5-methoxy-2,5-dihydrofuran-3-carbaldehyde (2 and 4) were synthesized in 60 and 15percent yield, respectively, by lithium bromide induced rearrangement of 6-O-silylated methyl 2,3- and 3,4-anhydro-α- and -β-D-hexopyranosides, obtained in two steps from methyl α- and β-D-glucopyranoside.Rearrangement of various other pento- and hexoside epoxides permitted the suggestion of probable reaction routes.Hydrogenation of the unsaturated aldehydes gave the corresponding saturated aldehydes in good yield.

Chiral Multifunctional Isoprene Units by Ring-Contraction of Riboside Oxiranes

Lithium bromide induced ring-contraction of benzyl 2,3- and 3,4-anhydro-β-D(and L)-ribopyranoside (1 and 4) in HMPA/toluene or tetramethylurea (TMU)/toluene gave (R)(and S)-2-(benzyloxy)-2,5-dihydrofufan-4-carboxaldehyde (2 and 5) together with a small amount of benzyl 4-bromo-4-deoxy-β-L(and D)-lyxopyranoside (3 and 6).The latter compound was formed with lithium bromide in 1,1,1-trichloroethane.Benzyl 2,3- and 3,4-anhydro-2-deuterio-β-L-ribopyranoside (4d and 8d) gave the deuterated aldehyde 5d, which carried a vinylic deuterium atom, wheraes benzyl 2,3-anhydro-4-deuterio-β-L-ribopyranoside (4d' ) gave the nondeuterated aldehyde 5.On the basis of these experiments, the mechanism of the ring-contraction as postulated.