Tetrahedron p. 3057 - 3074 (1996)
Update date:2022-07-30
Topics:
Dondoni, Alessandro
Marra, Alberto
Rojo, Isabel
Scherrmann, Marie-Christine
TMSOTf-promoted glycosidation of 1-C-(2-thiazolyl)-α-D-galactopyranosyl acetate (α)-2 and 1-C-(2-thiazolyl)-α-D-mannofuranosyl acetate 7 donors with 1 equiv of primary 3 and secondary 5 sugar alcohols acceptors gave exclusively the corresponding α-D-ketodisaccharides 4a, 8a, 11a, and 12a in 60-73% yield. On the other hand glycosidation of the 1-C-(2-thiazolyl)-α-D-glucopyranosyl acetate 6 with the primary alcohol 3 under the above conditions afforded a mixture of α- and β-D-ketodisaccharides 9a and 10a in ca. 1:1 ratio. The important role of the thiazole ring for the easy glycosidation of these ketol acetates was pointed out by comparison with ketoses bearing a methyl, carboxymethyl, and 2-furyl group. Application of the thiazolyl-to-formyl deblocking reaction sequence to the thiazolylketodisaccharides gave the corresponding aldehydes which in turn were converted into alcohols and esters by reduction and oxidation, respectively.
View MoreBinzhou Holly Pharmaceutical Co.,Ltd.
Contact:74517
Address:No.15 Dapu Road,Huangpu District Shanghai,P.R.China
JiYi Chemical (Beijing) Co., Ltd.
Contact:+86-10-89385733
Address:Shilou Town of Fangshan District, Beijing
Hunan Hui Bai Shi(YUNBANG)Biological Technology Co.,Ltd
website:http://www.hunanyunbang.com/
Contact:+86-731-85525605/+86-13319518603
Address:1103,C3 Building,No.27 Wenxuan Road, Yuelu District
Oren Hydrocarbons (Qingdao) Co., Ltd.
Contact:+86-532-68607667-801
Address:Room 3 # 302, No.9 Qingyun Road, Qingdao, China
website:http://www.uvchemkeys.com
Contact:0086-021-58785816
Address:RM2607 Building No.1 Guosheng, Lane 388, Zhongjiang Road, Putuo District, Shanghai 200062 China
Doi:10.1016/0020-1693(95)04760-3
(1996)Doi:10.1021/ja9541138
(1996)Doi:10.1016/j.tetlet.2017.02.015
(2017)Doi:10.1039/P19830001941
(1983)Doi:10.1080/00397919608002612
(1996)Doi:10.1021/ja00993a039
(1967)