Two optically active pseudo-hexopyranoses, pesudo-cl-Q--glucopyranose (1) and pseudo-B-&-altropyranose (11, were synthesized starting from &-araginose. converted to an acyclic aldehyde 2.dimethyl malonate under basic conditions provided a tetrahydroxylated cyclohexane-1,l-dicarboxylate 11 and a C-glycoside of B-L-arabinopyranose 12. From the compound 11, the desired two pseudo-sugars were synthesized by 1) thermal demethoxycarbonylation, 2 ) LiAl.H4 reduction, 3 ) hydroboration of the resulting I-hydroxymethyl-1-cyclohexene 14 followed by hydrogen peroxide treatment, and 4 ) removal of the protecting groups.

330ChemInform Abstract Starting with the trityl derivative (I) of L-arabinose, the iodide (IV) is prepared. It is cyclized with dimethyl malonate (V) and then acetylated, to yield the products (VII) and (VIII). (VII) is transformed into the allylic alcohol (IX) which is subjected to hydroboration and acetylation, producing the acetates (X) and (XI). These are deprotected to give the pseudo-α-D-glucopyranose (XIIb)and the pseudo-β-L-altropyranose (XIIIb) respectively.