Carbohydrate Research p. 135 - 148 (1989)
Update date:2022-09-26
Topics:
Rej, Rabindra N.
Glushka, John N.
Chew, Warren
Perlin, Arthur S.
In the chromate oxidation of a partially acylated sugar derivative to form the corresponding uronic acid, acyl migration to the primary alcohol group is a frequent cause of interference.In contrast to more commonly employed ester substituents, the O-levulinoyl group is far less prone to migration during oxidations with Jones reagent (chromic-sulfuric acids).Examples described here include levulinoyl at O-5 of acyclic and furanose derivatives, and both eq and ax O-4 of pyranose derivatives.It is also shown that, because of the acidity of the Jones reagent, use of the O-levulinoyl group, in combination with a primary p-anisyldiphenylmethyl substituent, permits sequential rapid hydrolysis of the latter and oxidation of the newly exposed alcohol group, which favors high overall yields.In contrast to its immobility in these oxidation reactions, when the leulinoyl group is on O-2 of an aldosyl bromide, it participates in 1,2-orthoester formation as rapidly as O-acetyl.The 2,3,4,6-tetraacetate of either anomer of methyl D-glucopyranoside is oxidized to a uronic acid in moderate yield, by chromic acid in 5:1 acetic acid-water.
View MoreTaizhou Chemedir Biopharm-tech Co., Ltd
Contact:+86 523 86200218
Address:G09, No. 1 Avenue China Medical City, Taizhou,Jiangsu, China
website:http://www.orchid-chem.com
Contact:+86-571-85395792
Address:607, North Zhongshan Road, Hangzhou 310000 China
Xi'an Unique Electronic and Chemical Co., Ltd.
Contact:+86-029-88238008
Address:1703# B BUILDING WEST ELECTRONIC ZONE, XI'AN, CHINA
wuxi huabin bio-tech Co.,Ltd(expird)
Contact:86-0510-85133006
Address:hubin road NO157
Shandong Hongxiang Zinc Co., Ltd
Contact:086-0311-66187879
Address:DaWang developing zone
Doi:10.1016/j.tet.2009.04.088
(2009)Doi:10.1021/ol901372m
(2009)Doi:10.1007/s11243-017-0148-6
(2017)Doi:10.1016/j.tetlet.2009.05.050
(2009)Doi:10.1021/ja01486a033
(1960)Doi:10.1021/jo9008832
(2009)