| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1346948 | Tetrahedron: Asymmetry | 2009 | 5 Pages |
The utility of the nitroaldol reaction for accessing 3-nitro-pyranoside, 3-nitro-septanoside or 4-nitro-septanoside derivatives, by reaction of the anion of nitromethane with glycoside dialdehydes is demonstrated. Initially, the feasibility of using unprotected glucoside dialdehydes was probed for the synthesis of the septanoside products, but this afforded pyranoside rather than septanoside targets. Subsequent studies utilised protected glycoside dialdehydes within the methodology, which allowed entry into a range of 3-nitro or 4-nitro-septanosides in good yield. NMR spectroscopic analysis allowed determination of the stereochemistry of each of the products thus afforded.
Graphical abstractThe utility of the nitroaldol reaction for accessing 3-nitro-pyranoside, 3-nitro-septansoide or 4-nitro-septanoside derivatives, by reaction of the anion of nitromethane with glycoside dialdehydes, is described.Figure optionsDownload full-size imageDownload as PowerPoint slide
Benzyl 3-deoxy-3-nitro-β-d-glucopyranosideC13H17NO7Ee = 100%[α]D20=-29.1 (c 1.01, MeOH)Source of chirality: methyl α-d-glucopyranoside
Methyl 5,7-O-benzylidene-3-deoxy-3-nitro-α-d-glycero-d-altro-septanosideC15H19NO8Ee = 100%[α]D20=+23.7 (c 1.75, MeOH)Source of chirality: methyl α-d-glucopyranoside
Methyl 2-O-benzyl-4-deoxy-4-nitro-7-benzyloxymethyl-α-d-glycero-l-manno-septanosideC22H27NO8Ee = 100%[α]D20=+96.9 (c 1.0, CHCl3)Source of chirality: methyl α-d-glucopyranoside
Methyl 2-O-benzyl-4-deoxy-4-nitro-7-benzyloxymethyl-α-d-glycero-d-talo-septanosideC22H27NO8Ee = 100%[α]D20=+49.4 (c 1.06, CHCl3)Source of chirality: methyl α-d-mannopyranoside
