Bhaumik, Atanu ; Pathak, Tanmaya (2015) Methyl-α-D-2-selenonyl pent-2-enofuranoside: a reactive selenosugar for the diversity oriented synthesis of enantiomerically pure heterocycles, carbocycles, and isonucleosides The Journal of Organic Chemistry, 80 (21). pp. 11057-11064. ISSN 0022-3263
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Official URL: http://pubs.acs.org/doi/abs/10.1021/acs.joc.5b0119...
Related URL: http://dx.doi.org/10.1021/acs.joc.5b01192
Abstract
The construction of vinyl selenone on a furanoside led to a highly reactive synthetic intermediate methyl-α-ᴅ-2-selenonyl pent-2-enofuranoside composed of a masked aldehyde, an electron-deficient double bond along with an excellent leaving group. This new Michael acceptor on reactions with different nucleophiles afforded bicyclic azasugars, cyclopropanated carbohydrate, dihydrofuran- and dihydroisoxazole- substituted furanosides, and isonucleosides in moderate to good yields. Hydrolysis of the hemiacetal linkage of some of these modified carbohydrates afforded enantiopure aziridines, nitrocyclopropane, and dihydrofuran.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 103715 |
| Deposited On: | 22 Mar 2017 05:34 |
| Last Modified: | 22 Mar 2017 05:34 |
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