Sugar nitromethane adducts

Bols [27] reported an improved synthesis of isofagomin 32 and noeuromycin 34 from D-ara-binose in six and seven steps, respectively. As shown in O Scheme 12, Henry reaction of ketone sugar 29 gave the nitromethane adduct benzyl 4-deoxy-4-C-nitromethylene-D-arabi-... 

After their preliminary studies on the conjugate addition of nitromethane to sugar-derived enoates,34 Costa et al. reported more exhaustive studies that include the addition of nitromethane to enoate 33 in the presence of TBAF, to give a mixture of the two adducts 34 and 35 (Scheme 13).35... 

The value of the 1,3-dithian route to branched-chain sugar derivatives has been illustrated further by stereospecific syntheses of 3-C-formyl, 3-C-hydroxymethyl, and 3-C-methyl derivatives of D-psicose from the ketone (373) via the dithianyl adduct (374). Addition of nitromethane to (373) gave both 3-C-nitromethyl-o-psicose and -fructose derivatives, which, after separation by chromatography, were reduced to the corresponding 3-C-aminomethyl derivatives. The use of dithianyl derivatives in the synthesis of streptomycin components is dealt with in Chapter 18. 

Branched-chain Sugars.- Methyl 6-deo -3- -methyl-a-L-mannopyranoside, the tricyclic lactone (10), the 3-carbo QrmethyI-3-deoxy-sugar (11), the adduct (12) from levoglucosenone and nitromethane, and the ( clobutanone derivative (13). ... 

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