Preparation and diastereomeric separation of an (S)- and (R)-1-(methoxycarbonyl)tridec-10-yl glucoside derivative, a precursor for a monosaccharide constituent of resin glycosides
Kobayashi, S; Furukawa, Ji; Sakai, T; Sakairi, N
| HERO ID | 5416782 |
|---|---|
| In Press | No |
| Year | 2002 |
| Title | Preparation and diastereomeric separation of an (S)- and (R)-1-(methoxycarbonyl)tridec-10-yl glucoside derivative, a precursor for a monosaccharide constituent of resin glycosides |
| Authors | Kobayashi, S; Furukawa, Ji; Sakai, T; Sakairi, N |
| Journal | Carbohydrate Research |
| Volume | 337 |
| Issue | 11 |
| Page Numbers | 1047-1053 |
| Abstract | The 6-O-mesyl derivative of phenyl 1-thio-beta-D-glucopyranoside was prepared from D-glucose as a synthetic equivalent of a 6-deoxy-hexosyl donor. Racemic methyl 11-hydroxytetradecanoate (methyl convolvulinolate) was synthesized by Grignard reaction of propylmagnesium bromide with 10-undecenal followed by hydroboration. Both intermediates were coupled by NIS-TfOH-promoted glycosidation to give a mixture of two diasteromeric glucopyranosides, which were separated on a preparative scale by medium pressure chromatography. One of the products was identified as having the natural (S)-configuration by comparison of its 1H NMR spectrum with an authentic sample prepared from the corresponding chiral hydroxyfatty acid. |
| Doi | 10.1016/s0008-6215(02)00092-7 |
| Pmid | 12039547 |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |
| Language Text | English |