108167-80-2Relevant academic research and scientific papers
Alkaline and Enzymatic Hydrolysis of Isobutyl 3,4-Anhydro-2,6-dideoxy-DL-hexopyranosides. Preparation of Enantiomeric Boivinopyranosides through a Highly Efficient Kinetic Resolution
Barili, Pier Luigi,Berti, Giancarlo,Catelani, Giorgio,Colonna, Fabrizia,Mastrorilli, Ettore
, p. 2886 - 2892 (1987)
Racemic isobutyl 3,4-anhydro-2,6-dideoxy-β-ribo-hexopyranoside and -lyxo-hexopyranoside have been prepared starting from the cycloadduct between 3-buten-2-one and isobutyl vinyl ether.Alkaline hydrolysis converted the lyxo isomer exclusively into isobutyl
PREPARATION OF ISOBUTYL 3,4-ANHYDRO-2,6-DIDEOXY-DL-α-LYXO-HEXOPYRANOSIDE AND ITS KINETIC RESOLUTION WITH MICROSOMAL EPOXIDE HYDROLASE.
Barili, Pier Luigi,Berti, Giancarlo,Catelani, Giorgio,Colonna, Fabrizia,Mastrorilli, Ettore,Paoli, Marco
, p. 1553 - 1566 (1989)
Racemic isobutyl 3,4-anhydro-2,6-dideoxy-α-lyxo-hexopyranoside, 3, was prepared starting from the cycloadduct between 3-buten-2-one and isobutyl vinyl ether, through a sequence involving hydroboration-oxidation, mesylation, anomeric equilibration, elimination and epoxidation.The intermediate isobutyl 2,3,4,6-tetradeoxy-α-3-DL-hexenopyranoside, 10 was not stable under the conditions used for its preparation (t-BuOK in DMSO), being converted in part into the corresponding 2-hexenopyranoside.Under the same conditions the α-anomer of 10 was stable.Comlete hydrolysis of DL-3 with aqueous NaOH, or with microsomial epoxide hydrolase (MEH) gave exclusively the xylo-diol (isobutyl DL-α-boivinopyranoside 5).When the hydrolylsis with MEH was stopped near 50percent conversion and the product diol was separated from the unchanged epoxide, both were optically active, the former having the L and the latter the D configuration.An ee of at least 96percent was found for both the diol and the epoxide by the use of a chiral shift reagent.
