Resin-linked glycosides

A synthesis of the branched chain nucleoside analogue precursor 32 has been prepared by sequential treatment of dimethyl (2S)(3S)-2-aIlyl-3-hydroxygIutarate (prepared by yeast reduction of dimethyl 2-allyl-3-oxogIutarate) with ozone, acid resin and methanol then LAH. Branched-chain nucleosides are covered in Ch ter 20 and the preparation of C-linked glycosides and nucleosides are mentioned in Chapters 3 and 20 respectively. 

Support-bound alcohols and thiols can be used to immobilize aldehydes and ketones as acetals. Mixed acetals of carbonyl compounds with support-bound alcohols can be prepared by transacetalization of a symmetric acetal under acidic conditions [719]. The formation of mixed acetals on solid phase is, however, not always easy to perform and control, and so prior preparation of a mixed acetal in solution followed by loading onto a support is often the preferred protocol [626,637]. Carbohydrates can be linked to resin-bound alcohols or thiols as glycosides (Table 3.40). 

In combinatorial chemistry, the development of multicomponent reactions leading to product formation is an attractive strategy because relatively complex molecules can be assembled with fewer steps and in shorter periods. For example, the Ugi multicomponent reaction involving the combination of an isocyanide, an aldehyde, an amine, and a carboxylic acid results in the synthesis of a-acyl amino amide derivatives [32]. The scope of this reaction has been explored in solid-phase synthesis and it allows the generation of a large number of compounds with relative ease. This reaction has been employed in the synthesis of a library of C-glycoside conjugated amino amides [33]. Scheme 14.14 shows that, on reaction with carboxylic acids 38, isocyanides 39, and Rink amide resin derivatized with different amino acids 40, the C-fucose aldehyde 37 results in the library synthesis of C-linked fucosyl amino acids 41 as potential mimics of sialyl Lewis. ... 

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