104292-62-8Relevant academic research and scientific papers
Ring opening reactions of benzyl 3,4-anhydro-β-D-ribopyranoside with nucleophiles
Vasudeva, Pejakala K.,Nagarajan, Madhavarao
, p. 1747 - 1766 (1996)
By the proper choice of metal counterion it is possible to regioselectively cleave with a variety of nucleophiles, the epoxide ring of benzyl 3, 4-anhydro-β-D-ribopyranoside. The resulting 3-deoxy 3-substituted or 4-deoxy 4-substituted glycosides were obtained in good yields. Factors governing the regiochemistry of ring opening are discussed.
Chiral Multifunctional Isoprene Units by Ring-Contraction of Riboside Oxiranes
Sundin, Anders,Frejd, Torbjoern,Magnusson, Goeran
, p. 3927 - 3930 (2007/10/02)
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.
