TY - JOUR
T1 - A stereoselective synthesis of xylitol
AU - Holland, David
AU - Stoddart, J. Fraser
PY - 1982
Y1 - 1982
N2 - Rel-(2S, 3R, 4R)- (6) and rel-(2R,3R,4R)- (7) 1,2,5-triacetoxy-3,4-epoxypentanes have been obtained in seven steps starting from cyclopentadiene. Both diastereoisomers afford xylitol pentaacetate (8) selectively upon epoxide cleavage with acetate ion. In the case of (6), rel-(1s,3R,4r,5S)-3,-bisacetoxymethyl-1-methyl-2,6,7-trioxabicyclo- [2.2.1]heptane (11) has been isolated and characterised as an intermediate in the reaction.
AB - Rel-(2S, 3R, 4R)- (6) and rel-(2R,3R,4R)- (7) 1,2,5-triacetoxy-3,4-epoxypentanes have been obtained in seven steps starting from cyclopentadiene. Both diastereoisomers afford xylitol pentaacetate (8) selectively upon epoxide cleavage with acetate ion. In the case of (6), rel-(1s,3R,4r,5S)-3,-bisacetoxymethyl-1-methyl-2,6,7-trioxabicyclo- [2.2.1]heptane (11) has been isolated and characterised as an intermediate in the reaction.
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U2 - 10.1016/S0040-4039(00)85841-4
DO - 10.1016/S0040-4039(00)85841-4
M3 - Article
AN - SCOPUS:0020362703
SN - 0040-4039
VL - 23
SP - 5367
EP - 5370
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 50
ER -