Stereo-controlled approach to pyrrolidine iminosugar C-glycosides and 1,4-dideoxy-1,4-imino-L-allitol using a D-mannose-derived cyclic nitrone
| Title | Stereo-controlled approach to pyrrolidine iminosugar C-glycosides and 1,4-dideoxy-1,4-imino-L-allitol using a D-mannose-derived cyclic nitrone |
| Publication Type | Journal Article |
| Year of Publication | 2009 |
| Authors | Bande, OP, Jadhav, VH, Puranik, VG, Dhavale, DD, Lombardo, M |
| Journal | Tetrahedron Letters |
| Volume | 50 |
| Issue | 49 |
| Pagination | 6906-6908 |
| Date Published | DEC |
| ISSN | 0040-4039 |
| Keywords | Cyclic nitrone, Enzyme inhibitors, Iminosugars, pyrrolidine |
| Abstract | Intramolecular N-alkylation of 2,3-O-isopropylidene-5-O-methanesulfonyl-6-O-t-butyldimethylsilyl-D-mann ofuranose-oxime 7 afforded a five-membered cyclic nitrone 9, which on N-O bond reductive cleavage followed by deprotection of -OTBS and acetonide functionalities gave 1,4-dideoxy-1,4-imino-L-allitol (DIA) 3. Addition of allylmagnesium chloride to nitrone 9 afforded alpha-allylated product 10a in high diastereoselectivity providing an easy entry to N-hydroxy-C1-alpha-allyl-substituted pyrrolidine iminosugar 4a after removal of protecting group, while N-O bond reductive cleavage in 10a afforded C1-alpha-allyl-pyrrolidine iminosugar 4b. (C) 2009 Elsevier Ltd. All rights reserved. |
| DOI | 10.1016/j.tetlet.2009.09.139 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 2.618 |
Divison category:
Center for Material Characterization (CMC)