Tetrahedron p. 1553 - 1566 (1989)
Update date:2022-08-11
Topics:
Barili, Pier Luigi
Berti, Giancarlo
Catelani, Giorgio
Colonna, Fabrizia
Mastrorilli, Ettore
Paoli, Marco
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.
View MoreSuzhou Credit International Trading Co., Ltd
Contact:+86-512-65398039
Address:Qingdeng, Hightech. District, Suzhou
website:http://www.debyesci.com
Contact:+85221376140
Address:Rm. 19C, Lockhart Ctr., 301-307 Lockhart Rd., Wan Chai
Contact:0086-22-2822 1962 / 2822 1963
Address:B-808, No. 1, North-South Street, Hexi District,
Hunan Shineway Enterprise Co., Ltd.
Contact:+86-731-86303875
Address:118, Huanghua International Airport Road, Huanghua Town, Changsha, Hunan 410137, China
Contact:+86-519-86623222
Address:29F/D, 99 Yanling West Road, Changzhou, Jiangsu, China
Doi:10.1016/j.tetlet.2008.08.013
(2008)Doi:10.1055/s-0034-1380538
(2015)Doi:10.1016/j.catcom.2014.09.036
(2015)Doi:10.1039/jr9370001559
(1937)Doi:10.1016/j.tetlet.2004.09.005
(2004)Doi:10.1055/s-2006-948205
(2006)