51267-44-8Relevant articles and documents
Whistler,Be Miller
, p. 3705 (1960)
A highly diastereoselective synthesis of 4-octulose and 2-deoxy-4-octulose from a D-fructose derivative
Izquierdo, Isidoro,Plaza, Maria T.,Robles, Rafael,Rodriguez, Concepcion
, p. 3593 - 3604 (2007/10/03)
Bishydroxylation of methyl (Z)-2,3-dideoxy-4,5:6,7-di-O-isopropylidene-β-D- arabino-oct-2-ene-4-ulo-4,8-pyranosonate 1 with osmium tetraoxide proceeded with extremed high diastereoselectivity to give only methyl 4,5:6,7-di-O-isopropylidene-β-D-arabino-L-erythro-oct-4-ulo-4,8-pyranosonate 2. Configurations of the new stereogenic centers (C-2,3) in 2 were determined by degradation of the C-5,6,7,8 fragment to the well-known methyl 2,3,4-tri-O-methyl-D-(+)-erythronate 7. Transformation of 2 into the required D-arabino-L-erythro-oct-4-ulosa 10, was achieved by a methodology that implied, protection to 8, reduction of the ester group in 8 to a hydroxymethyl group in 9, and finally deprotection to the free D-arabino-L-erythro-oct-4-ulosa 10. On the other hand, epoxidation reaction on (E)-2,3-dideoxy-4,5:6,7-di-O-isopropylidene-β-D-arabino-oct-2-ene-4-ulo-4,8 -pyranose 11 afforded only the corresponding 2,3-anhydro derivative 12 with β-D-arabino-D-threo configuration, as could be demonstrated by degradation to (S)-1,2,4-trimetoxybutane 16, which synthesis is reported herein.
Enantioselective Synthesis of (S)- and (R)-6-(2,3-Dihydroxypropyl)-1,3-dioxin-4-ones: the Versatile Building Blocks of Four- and Six-carbon Backbones
Sakaki, Jun-ichi,Sugita, Yoshiaki,Sato, Masayuki,Kaneko, Chikara
, p. 434 - 435 (2007/10/02)
The Sharpless asymmetric epoxidation of 2,2-dimethyl-6-(3-hydroxy-1-propenyl)-1,3-dioxin-4-one using titanium tetraisopropoxide-diisopropyl tartrate followed by catalytic hydrogenation affords the title compounds as enantiomerically pure compounds, which act as versatile four- and six-carbon building blocks.
