Helvetica Chimica Acta p. 1738 - 1746 (1995)
Update date:2022-08-04
Topics:
Granier
Vasella
The (1H-imidazol-2-yl)ulose 8 and the 1H-imidazol-2-yl C-glycopyranosides 23 and 24 have been prepared from tetra-O-benzylgluconolactone 6 in two and six steps, respectively. The imidazoles 8 and 24 are moderate competitive inhibitors of sweet-almond β-glucosidase (pH 6.8, K(i) ~ 0.79 and 0.64 mM, respectively), while 23 is a competitive inhibitor of yeast α-glucosidase (pH 6.8, K(i) ~ 0.26 mM). Addition of 2-lithiated 1-[(dimethylamino)methyl]-1H-imidazole to 6 gave the ulose 7 (68%), which was deprotected to 8. Reduction of 7 with NaBH4 yielded a 12:88 mixture 10/11. Attempts to selectively mesylate HO-C(1) of these diols failed, while dinitrobenzoylation led to 19/20, which cyclized easily (NaH) to a 25 :75 mixture of 21 and 22 which were separated and debenzylated to the C-glycosides 23 and 24.
View Morewebsite:http://www.sagechem.com
Contact:+86-571-86818502
Address:Room C1301, New Youth Plaza, 8 Jia Shan Road, Hangzhou, China
Contact:86-513-84128750/13773795976
Address:No.48.Youyi West Road ,Rudong Development Zone,Jiangsu Province,China
Shanghai Yuantai Chemical Products Co., Ltd
Contact:021--66129803
Address:Chengyin Road,Shanghai,China
website:http://www.lidepharma.com
Contact:+86-25-58409506
Address:11F, Building A1, No.288 North Zhongshan Road, Gulou District, Nanjing,210003, P.R.China.
Rugao Jinling Chemical Co., Ltd.(expird)
Contact:0086-513-68005586
Address:Lianluo new village huangshi town Rugao city Jiangsu Province.
Doi:10.1039/b310843k
(2003)Doi:10.1016/S0022-1139(00)82844-4
(1978)Doi:10.1016/0039-128X(77)90066-6
(1977)Doi:10.1021/ja01017a037
(1968)Doi:10.1016/j.ica.2003.11.002
(2004)Doi:10.1016/S0020-1693(00)86249-0
(1977)