Journal of Carbohydrate Chemistry p. 99 - 115 (1998)
Update date:2022-08-04
Topics:
Boissière-Junot, Nathalie
Tellier, Charles
Rabiller, Claude
With the aim of providing new methods for the regioselective protection at the 2,3 and 4 positions of monosaccharides, we have studied the acetylation of a class of rigid sugars: the 1,6-anhydro-β-D- and L-hexopyranoses (hexopyranosanes D-1 to D-5 and L-1 to L-5), using vinyl acetate as an acyl donor and two common lipases,Candida rugosa and Pseudomonas cepacia, as catalysts. Our results indicate that the relative orientation of the hydroxyls governs the regioselectivity of acetylation. In the D-series, when the 3-OH is in the axial position, acetylation occurs mainly at the 4-axial OH, while the 2-axial OH is preferred when the 4-OH is equatorial. Conversely, when the 3-OH is equatorial, a strong selectivity affects the equatorial 2-OH. Compounds of the L-series were shown to be poor substrates for the lipase Pseudomonas cepacia except for L-galactosane for which the 2-monoacetyl ester was obtained in good yield. An attempt to rationalize the results by means of molecular modelling is also made to account for the catalytic activity of the Candida rugosa lipase on hexopyranosanes 1-3.
View MoreContact:86-21-50966856
Address:Building 5,300 Chuanzhan Road,Pudong New District,Shanghai
Anhui Sholon New Material Technology Co., Ltd.
website:http://www.sholonchem.com
Contact:+86-550-5261666
Address:4/F Block B, Beijing Chemical Building.No.520 Tianrun Road ,Science & Education Town Wujin District, Changzhou City Jiangsu Province
A.M FOOD CHEMICAL CO., LIMITED
Contact:86-531-87100375
Address:20Floor,Bblock,1Building,pharma-valley,Jinan,China
Lishui Nanming Chemical Co., Ltd(expird)
Contact:+86-0578-2134101,2697830
Address:No.19 Tongji Road Shuige Industrial zone
Shanghai doly chemical Co.,Ltd
Contact:+86-21-34716221
Address:No.328,WuHe Roard,MinHang,ShangHai China
Doi:10.1021/ja074044k
(2008)Doi:10.1021/ol800053f
(2008)Doi:10.1515/znb-2007-0323
(2007)Doi:10.1039/c5nj01507c
(2015)Doi:10.1039/c6ra00738d
(2016)Doi:10.1016/0040-4020(96)00165-2
(1996)