Sugars from glycals

S. Sabesan and S. Neira, Synthesis of 2-deoxy sugars from glycals, J. Org. Chem., 56 (1991) 5468-5472. 

Murali, R, Ramana, C V, Nagarajan, N, Synthesis of 1,2-cyclopropanated sugars from glycals, J. Chem. Soc. Chem. Common., 217—218, 1995. 

A new stereoselective diesis of 1,2-anhydro-sugars from glycals has been reported (Scheme 3). Although little selectivity is observed in die initial bromohydrin formation, die resulting... 

Figure 2.4 Synthesis of glycosyl fluorides from 1,2-anhydro sugars and glycal derivatives.

The azidonitration route to 2-amino-2-deoxy sugars from D-glycal should be compared with the alternative route exploiting the addition of nitrosyl chloride (Section 7.2.1.1). Both methods have been tested on the synthesis of intermediates of D-lactosamine, and the azidonitration method was considered more efficient95. 

However, the demonstration that 1,2-anhydro sugars are readily obtained from glycals by treatment with dimethyldioxirane led to a renaissance of their use in glycoside synthesis and, indeed, in solution-phase and solid-phase oligosaccharide synthesis.182... 

The synthesis and use of glycal derivatives in the preparation of staurosporine and en/-staurosporine is mentioned in Chapter 24 and an investigation into the isomerization of 2-oxo-pyranosides in pyridine affording a hydroxyenone product is covered in Chapter 15. The synthesis of a 1,2-unsaturated C-2 branched, 3,4-annulated sugar from a 2,3-unsaturated pyranose bearing a 4-0-allyl substituent is covered in Chapter 14. 

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