Unusual addition of amines to C-2 of vinyl sulfone-modified-beta-D-pent-2-enofuranosyl carbohydrates: synthesis of a new class of beta-anomeric 2-amino-2,3-dideoxy-D-threo-pentofuranosides
| Title | Unusual addition of amines to C-2 of vinyl sulfone-modified-beta-D-pent-2-enofuranosyl carbohydrates: synthesis of a new class of beta-anomeric 2-amino-2,3-dideoxy-D-threo-pentofuranosides |
| Publication Type | Journal Article |
| Year of Publication | 2008 |
| Authors | Das, I, Suresh, CG, Decout, J-L, Pathak, T |
| Journal | Carbohydrate Research |
| Volume | 343 |
| Issue | 8 |
| Pagination | 1287-1296 |
| Date Published | JUN |
| Type of Article | Article |
| ISSN | 0008-6215 |
| Keywords | amino sugars, deoxyaminosugars, desulfonylation with Mg-MeOH-NiBr(2), diastereoselective Michael addition, vinyl sulfone-modified carbohydrates |
| Abstract | When 3-C-sulfonyl-pent-2-enofuranosides and 3-C-sulfonyl-hex-2-enofuranosides were reacted with primary and secondary amines, only the beta-anomeric methoxy group of the pent-2-enofuranoside did not cause any hindrance to incoming nitrogen nucleophiles. This resulted in the `unusual' addition of amines, in which the diastereoselectivity of the reaction was overwhelmingly in favor of amino sugars of the D-arabino configuration. Selected products were desulfonylated to obtain a new class of beta-anomeric 2-amino-2,3-dideoxy-D-threo-pentofuranosides. (C) 2008 Elsevier Ltd. All rights reserved. |
| DOI | 10.1016/j.carres.2008.03.022 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 1.817 |
Divison category:
Biochemical Sciences