ChemInform Abstract: SYNTHESE VON AMIDANALOGEN DES GLUCOSE‐6‐PHOSPHATS

Abstract

1,2:3,5‐Di‐O‐isopropyliden‐D‐glucofuranose (I) und l,2:3,4‐Di‐O‐isopropyliden‐D‐galaktopyranose (IV) werden mit Hilfe von Hexamethyltriamidophosphit (II) in 6‐Ste1lung phosphoryliert, man erhält die Phosphite (III) und (V).

Amides of Trivalent Phosphorus Acids as Phosphorylating Reagents for Proton-Donating Nucleophiles

“…Phosphorus triamides phosphorylate efficiently monosaccharides, whose molecules contain one free alcoholic hydroxyl, − for example, 1,2:3,5-diisopropylidene- d -glucofuranose (Scheme ) 76 …”

“…The fact that phosphorylation by ATPA allows introduction into carbohydrate molecules of phosphorus-containing groups having various substituents at the phosphorus atom, which influence the reactivity of phosphorus in various transformations, is also significant. 440 Phosphorus triamides phosphorylate efficiently monosaccharides, whose molecules contain one free alcoholic hydroxyl, [441][442][443][444] for example, 1,2:3,5-diisopropylidene-D-glucofuranose (Scheme 76). 441 Phosphorylation by dialkyl 322 or alkanediyl phosphoramidites, 445 phosphonamidites, 446 and phosphinamidites 447 follows a similar pathway.…”

“…440 Phosphorus triamides phosphorylate efficiently monosaccharides, whose molecules contain one free alcoholic hydroxyl, [441][442][443][444] for example, 1,2:3,5-diisopropylidene-D-glucofuranose (Scheme 76). 441 Phosphorylation by dialkyl 322 or alkanediyl phosphoramidites, 445 phosphonamidites, 446 and phosphinamidites 447 follows a similar pathway. In the case where two or three moles of a monosaccharide per mole of the phosphorylating reagent are introduced into the reaction, di-and triglycophosphites or -phosphonites can be formed (Scheme 77).…”