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Stereoselective synthesis of [13C]methyl 2-[15N]amino-2-deoxy-beta-D-glucopyranoside derivatives.
| Content Provider | Semantic Scholar |
|---|---|
| Author | Boulineau, Fabien P. Wei, Alexander J. |
| Copyright Year | 2001 |
| Abstract | Efficient syntheses of three [13C]methyl 2-[15N]amino-2-deoxy-beta-D-glucopyranoside derivatives are described. Amination of the D-glucal with (saltmen)Mn(15N) proceeded with 11:1 stereoselectivity favoring the gluco configuration; subsequent methylation of the [15N]lactol using [13C]iodomethane and silver(I) oxide afforded the doubly labeled beta glucoside in high yield. This compound served as the common precursor for three [13C]methyl 2-[15N]aminoglucosides: (2-[15N]trifluoroacetyl-), (2-[15N]acetyl-), and (2-[15N]azido-). Selected heteronuclear coupling constants are reported. |
| File Format | PDF HTM / HTML |
| DOI | 10.1016/S0008-6215(01)00203-8 |
| Alternate Webpage(s) | http://www.chem.purdue.edu/awei/publications/boulineau1.pdf |
| PubMed reference number | 11527528 |
| Alternate Webpage(s) | https://doi.org/10.1016/S0008-6215%2801%2900203-8 |
| Journal | Medline |
| Volume Number | 334 |
| Issue Number | 4 |
| Journal | Carbohydrate research |
| Language | English |
| Access Restriction | Open |
| Content Type | Text |
| Resource Type | Article |