Solid phase synthesis glycoside

S. Hanessian, B. Lou, and H. Wang, Synthesis of (7-glycosides on solid phase utilizing 3 methoxy-2-pyridyloxy glycosyl donors, unpublished results S. Hanessian, Sterecontrolled glycosidation, Canadian patent applied for July 19, 1993. 

Scheme 14 Application of -pentenyl glycosides to solid phase synthesis preparation of a trisaccharide.

Scheme 5.63 Use of glycals in solid-phase synthesis of glycosides.

The fhioethyl group present in the anchor group of (40) was activated by treatment with N-iodosuccinimide (NIS) followed by displacement with a variety of alcohols (44-46). To prove the possible application of this linker in solid phase carbohydrate synthesis, protected glycosides (47) and (48) were coupled to linker (40) and released enzymatically. Flitsch et al. also described the immobilization and enzymatic cleavage on a variety of amines [41]. Nevertheless, the application of this enzyme-labile hnker group in multi-step syntheses on the solid phase and subsequent enzyme-initiated release from the polymeric support has not been described yet. 

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