Compounds with an R-C-N Branch

The synthesis of a vancosamine derivative by the rearrangement of a trichloroacetimidate of a branched-chain unsaturated sugar is mentioned in Chapter 13. 

The isomeric 2-deoxy-2-C-methyl-pentonic acids (34) have been prepared by Lewis acid-catalysed aldol condensation of the thioester silyl ketene acetal (35) with 2,3-di-O-benzyl-D-glyceraldehyde either epimer can be obtained as the major product depending on the precise experimental procedure adopted. 

The hetero-substituted alkene (36) obtained from a C-6 sugar aldehyde undergoes stereo-controlled methyl addition via the 

Thiem s group has investigated the synthesis and thermal reactions of branched-chain unsaturated sugars. The mycaroside (42) undergoes elimination with thionyl chloride to give the unsaturated 

Related results with glycosyl sulphones are referred to in 

A note has been published on the conversion of an acetamido branched-chain sugar derivative to the corresponding nitro analogue (L-decilonitrose) by sequential N-deacetylation using calcium in liquid ammonia followed by m-chloroperbenzoic acid oxidation. Syntheses of D- and L-rubranitrose by Brimacombe s group are mentioned in Chapter 10, and the synthesis of 3 -C-methyldauno-rubicin (containing vancosamine) is covered in Chapter 19. 

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Branched-chain Sugars Compounds with an R-C-0 Branch Compounds with an r-C-N Branch... 

The synthesis of evemitrose glycosides is mentioned in Chapter 3. See also Scheme xeceding section, for the preparation of a compound with an R-C-N branch. 

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