| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1346007 | Tetrahedron: Asymmetry | 2012 | 5 Pages |
The reaction of 2,3:4,5-diacetone-d-arabinose with protected dihydroxyacetone catalyzed by l-proline afforded two diastereoisomeric octoses in a 7:1 ratio in 75% yield. The anti (3S,4S) configuration at the newly created stereogenic centers was assigned to the main isomer on the basis of the X-ray analysis. The same reaction when catalyzed with unnatural d-proline provided the same products in a 1:20 ratio.
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1,3:5,6:7,8-Tri-O-isopropylidene-2,4-O-carbonate-d-erythro-l-galacto-octitolC18H28O9[α]Drt=+25.2 (c 1, CHCl3)Source of chirality: organocatalytic reactionAbsolute configuration: (2R,3R,4R,5R,6S,7R)
2,4-Di-O-carbonate-1,3:5,6:7,8-tri-O-isopropylidene-d-erythro-l-talo-octitolC18H23O9[α]Drt=+24.3 (c 1, CHCl3)Source of chirality: organocatalytic reactionAbsolute configuration: (2S,3R,4R,5R,6S,7R)
1,3:5,6:7,8-Tri-O-isopropylidene-d-glycero-d-talo-oct-2-uloseC17H28O8[α]Drt=-74.3 (c 1, CHCl3)Source of chirality: organocatalytic reactionAbsolute configuration: (3S,4S,5R,6S,7R)
4-O-(tert-Butyl-dimethylsilyl)-1,3:5,6:7,8-tri-O-isopropylidene-d-glycero-d-talo-oct-2-uloseC23H42O8Si[α]Drt=-93.1 (c 1, CHCl3)Source of chirality: organocatalytic reactionAbsolute configuration: (3S,4S,5R,6S,7R)
1,3:5,6:7,8-Tri-O-isopropylidene-d-glycero-d-gulo-oct-2-uloseC17H28O8[α]Drt=+99.6 (c 1, CHCl3)Source of chirality: organocatalytic reactionAbsolute configuration: (3R,4R,5R,6S,7R)
