| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1344840 | Tetrahedron: Asymmetry | 2009 | 6 Pages |
New asymmetric syntheses of (−)-methyl shikimate 1 and (−)-5a-carba-β-d-gulopyranose 11 from d-arabinose through a common route which employed Mukaiyama-type intramolecular aldolization as a key step were described.
Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slide
(−)-Methyl shikimateC8H12O5[α]D25=-131.5 (c 0.75, EtOH)Source of chirality: d-arabinoseAbsolute configuration: (3R,4S,5R)
(E)-(4R,5S,6R)-Ethyl 4,5,6,7-tetrahydroxy-hept-2-enoateC9H16O6[α]D25=+15.1 (c 0.4, MeOH)Source of chirality: d-arabinoseAbsolute configuration: (4R,5S,6R)
(4R,5S,6R)-Ethyl 4,5,6,7-tetrahydroxy-heptanoateC9H18O6[α]D25=+9.2 (c 0.5, H2O)Source of chirality: d-arabinoseAbsolute configuration: (4R,5S,6R)
(4R,5S,6R)-Ethyl 4,5,6-trihydroxy-7-triphenylmethoxy-heptanoateC28H32O6[α]D25=+6.8 (c 2.6, EtOAc)Source of chirality: d-arabinoseAbsolute configuration: (4R,5S,6R)
(−)-Methyl 3,4,5-O-triacetyl shikimateC14H18O8[α]D25=-172.4 (c 0.47, CHCl3)Source of chirality: d-arabinoseAbsolute configuration: (3R,4S,5R)
(4R,5S,6R)-5,6-Diallyloxy-7-triphenylmethoxy-heptano-1,4-lactoneC32H34O5[α]D25=-5.7 (c 3, EtOAc)Source of chirality: d-arabinoseAbsolute configuration: (4R,5S,6R)
(4R,5S,6R)-5,6-Diallyloxy-7-hydroxy-heptano-1,4-lactoneC13H20O5[α]D25=-37.5 (c 1.4, EtOAc)Source of chirality: d-arabinoseAbsolute configuration: (4R,5S,6R)
(1S,2S,3S,4S,5R)-2-(tert-Butyldimethylsilyloxy)-3,4-diallyloxy-6-oxa-bicyclo[3,2,1]octan-7-oneC19H32O5Si[α]D25=+56.0 (c 1.05, EtOH)Source of chirality: d-arabinoseAbsolute configuration: (1S,2S,3S,4S,5R)
(1S,2S,3R,4S,5R)-Methyl 2,3,4,5-tetraacetoxy-cyclohexanecarboxylateC16H22O10[α]D25=-3.3 (c 1.5, CHCl3)Source of chirality: d-arabinoseAbsolute configuration: (1S,2S,3R,4S,5R)
(1R,2S,3R,4S,5R)-5-Hydroxymethyl-cyclohexane-1,2,3,4-tetrolC7H14O5[α]D25=-58.3 (c 0.4, MeOH)Source of chirality: d-arabinoseAbsolute configuration: (1R,2S,3R,4S,5R)
(1R,2S,3S,4S,5R)-4-(tert-Butyldimethylsilyloxy)-2,3-diallyloxy-5-hydroxymethyl cyclohexanolC19H36O5Si[α]D25=-38.3 (c 1.2, EtOH)Source of chirality: d-arabinoseAbsolute configuration: (1R,2S,3S,4S,5R)
(1R,2S,3R,4S,5R)-5-Acetoxymethyl-1,4-diacetoxy-2,3-diallyloxy-cyclohexaneC19H28O8[α]D25=-43.7 (c 1.1, MeOH)Source of chirality: d-arabinoseAbsolute configuration: (1R,2S,3R,4S,5R)
(1R,2S,3R,4S,5R)-1,2,3,4-O-Tetraacetyl-5-acetoxymethyl-cyclohexane-1,2,3,4-tetrolC17H24O10[α]D25=-22.3 (c 1, CHCl3)Source of chirality: d-arabinoseAbsolute configuration: (1R,2S,3R,4S,5R)
