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1. (Article ID: 1619)
 
Guzlek H, Graziani A, Kosma P
A short synthesis of D-glycero-D-manno-heptose 7-phosphate
Carbohydrate Research 340(18) (2005) 2808-2811
 

d-glycero-d-manno-Heptopyranose 7-phosphate-an intermediate in the biosynthesis of nucleotide-activated heptoses-has been prepared in good overall yield from benzyl 5,6-dideoxy-2,3-O-isopropylidene-α-D-lyxo-(Z)-hept-5-enofuranoside by a short-step synthesis. Phosphitylation using the phosphoramidite procedure followed by in situ oxidation afforded the corresponding 7-O-phosphotriester derivative in high yield. Subsequent osmylation proceeded in good diastereoselectivity (4:1) to furnish the d-glycero-d-manno-configured derivative, which was separated from the l-glycero-l-gulo-isomer by chromatography. Hydrogenolysis led to simultaneous removal of the benzyl and isopropylidene groups and afforded the target compound in high yield, which serves as a substrate of bacterial heptose 7-phosphate kinases

biosynthesis, synthesis, heptose, intermediate, chemistry, Bacterial, group, high, derivative, D-glycero-D-manno-heptose, natural, chromatography, substrate, oxidation, target, removal, in situ, kinase

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