THE REACTION OF UNSATURATED CARBOHYDRATES WITH CARBON MONOXIDE AND HYDROGEN: IV. STRUCTURE AND STEREOCHEMISTRY OF ANHYDRODEOXYHEPTITOLS FROM 3,4,6-TRI-O-ACETYL-D-GALACTAL

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Abstract
3,4,6-Tri-O-acetyl-D-galactal reacted with carbon monoxide and hydrogen in the presence of dicobalt octacarbonyl to yield 2,6-anhydro-3-deoxy-D-galacto-heptitol (I) and 2,6-anhydro-3-deoxy-D-talo-heptitol (II). The stereochemistry of (I) and (II) has been established by correlation with 2,6-anhydro-3-deoxy-D-gluco-heptitol (VI) of known configuration. Evidence that both (I) and (II) are formed by the addition of a hydroxmethyl group to C-1 of the glycal is also furnished by the proton n.m.r. spectra of the normal and deuterated anhydrodeoxyheptitols.