| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1344756 | Tetrahedron: Asymmetry | 2010 | 4 Pages |
The synthesis of methyl α- and β-d-2,3-dideoxyriboside from a non-carbohydrate source is presented. The source of chirality is the microbial oxidation of halobenzenes to produce cyclohexadienediols, which are transformed into the final product in five steps with high chemical and enantiomeric purity.
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide
Methyl β-d-2,3-dideoxyribosideC6H12O3Ee = >99%[α]D23=-115 (c 0.1, CHCl3)Source of chirality: microbial oxidationAbsolute configuration: (1R,4S)
Methyl α-d-2,3-dideoxyribosideC6H12O3Ee = >99%[α]D23=+142 (c 0.2, CHCl3)Source of chirality: microbial oxidationAbsolute configuration: (1S,4S)
Methyl α-d-2,3-dideoxyglucofuranosideC7H14O4Ee = >99%[α]D23=+45 (c 0.8, CHCl3)Source of chirality: microbial oxidationAbsolute configuration: (1S,4S,5R)
Methyl β-d-2,3-dideoxyglucofuranosideC7H14O4Ee = >99%[α]D23=-37 (c 0.9, CHCl3)Source of chirality: Microbial oxidationAbsolute configuration: (1R,4S,R)
Methyl β-d-5,6-O-diacetyl-2,3-dideoxyglucofuranosideC11H18O6Ee = >99%[α]D23=-21 (c 0.9, CHCl3)Source of chirality: Microbial oxidationAbsolute configuration: (1R,4S,5R)
Methyl α-d-5,6-O-diacetyl-2,3-dideoxyglucofuranosideC11H18O6Ee = >99%[α]D23=+50 (c 0.9, CHCl3)Source of chirality: Microbial oxidationAbsolute configuration: (1S,4S,5R)
