Glucose derivatives syntheses starting from

L-Ascorbic acid biosynthesis in plants and animals as well as the chemical synthesis starts from D-glucose. The vitamin and its main derivatives, sodium ascorbate, calcium ascorbate, and ascorbyl palmitate, are officially recognized by regulatory agencies and included in compendia such as the United S fates Pharmacopeia/National Formula (USP/NF) and the Food Chemicals Codex (FCC). 

Scheme 24 Asymmetric synthesis of cw-P-lactams starting from chiral imines derived from D-(+)-glucose...

Apart from dehydration of glucose or fructose in the presence of alcohols and acid catalysts, synthesis strategies via 5-(chloromethyl)furfural and subsequent heating in the desired alcohol or utilizing furfuryl alcohol as feedstock have been demonstrated [89-98], While 5-(chloromethyl)furfural may be derived in one step based on cellulose, a synthesis procedure starting from furfuryl alcohol utilizes hemicellulose as feedstock, bridging the C5 and C6 carbohydrate value chain. 

The total synthesis of (+)-cyclophellitol containing a fully oxygenated cyclohexane ring was accomplished by T. Ishikawa and co-workers. The synthetic strategy was based on the intramolecular silyl nitronate [3+2] cycloaddition reaction. The cycloaddition precursor was prepared by the Henry reaction starting from a D-glucose-derived aldehyde. 

The pyranosidic homologation strategy has been also applied to the synthesis of compound (114) [196a,b], which also contains the nine stereocenters of streptovaricin A ansa chain (Scheme 50). Compound (114) was prepared starting from a D-glucose derivative, after conversion into a dipyranoside [196a] and thence tripyranoside [196d]. 

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