104292-75-3

Upstream product

• 104322-44-3 C₁₉H₂₁⁽²⁾HO₇S 
• 65247-32-7 benzyl 3,4-O-(1-methylethylidene)-β-L-erythro-pent-2-ulosylpyranoside 
• 18403-22-0 (3aS,6S,7R,7aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol 
• 104292-73-1 benzyl 2-deuterio-3,4-O-isopropylidene-β-L-arabinopyranoside 
• 104292-74-2 C₂₂H₂₅⁽²⁾HO₇S 

Downstream Products

• 104292-76-4 2(S)-(benzyloxy)-3-deuterio-2,5-dihydrofuran-4-carboxaldehyde 
• 104322-43-2 benzyl 3,4-anhydro-2-deuterio-β-L-ribopyranoside 

Relevant academic research and scientific papers

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.