Regioselective synthesis of alditol vicinal bis-cyclic thionocarbonates via alditol stannylene acetal complexes as a short and efficient route to alpha,omega-diiodoalditol derivatives.
The bis-cyclic thionocarbonates of alditols (pentitols and hexitols) were quickly and easily obtained from alditol stannylene complexes and phenyl chlorothionoformate (PhOC(S)Cl) in good yields. Acetylation of isolated free alditol bis-thionocarbonates and subsequent iodination using methyl iodide under pressure led to alpha,omega-diiodo derivatives of alditols in good to excellent isolated yields (67-93%).
Halila
Sami
S
Laboratoire des Glucides, Université de Picardie Jules Verne, 33 rue Saint-Leu, F-80039 Amiens, France.
Benazza
Mohammed
M
Demailly
Gilles
G
D000107:Acetylation; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D007294:Inositol / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D013402:Sugar Alcohols / Q000737:chemistry*
C452020:1,2-5,6-di-O-isopropylidene-myo-inositol; C452021:6-O-benzoyl-1,2-4,5-di-O-isopropylidene-myo-inositol; D019086:Bridged Bicyclo Compounds, Heterocyclic; D013402:Sugar Alcohols; D007294:Inositol