Aravind, Appu ; Sankar, Muthukumar Gomathi ; Varghese, Babu ; Baskaran, Sundarababu (2009) Regioselective reductive cleavage of bis-benzylidene acetal: stereoselective synthesis of anticancer agent OGT2378 and glycosidase inhibitor 1,4-dideoxy-1,4-imino-l-xylitol The Journal of Organic Chemistry, 74 (7). pp. 2858-2861. ISSN 0022-3263
Full text not available from this repository.
Official URL: http://pubs.acs.org/doi/full/10.1021/jo900030p
Related URL: http://dx.doi.org/10.1021/jo900030p
Abstract
A highly regioselective reductive cleavage of the bis-benzylidene acetal of d-mannitol was performed using a BF3·Et2O/Et3SiH reagent system. A chiral intermediate 6 thus obtained was efficiently utilized in the stereoselective synthesis of the anticancer agent OGT2378 (3) and glycosidase inhibitor derivative N-tosyl 1,4-dideoxy-1,4-imino-l-xylitol (22). Chemoselective reduction of azido epoxide 10 followed by regioselective intramolecular cyclization of amino epoxide 11 resulted in the exclusive formation of deoxyidonojirimycin derivative 12. By changing the order of deprotection, the chiral intermediate 6 was readily transformed to glycosidase inhibitor derivative 22.
Item Type: | Article |
---|---|
Source: | Copyright of this article belongs to American Chemical Society. |
ID Code: | 100065 |
Deposited On: | 27 Nov 2016 13:32 |
Last Modified: | 27 Nov 2016 13:32 |
Repository Staff Only: item control page