79386-44-0Relevant academic research and scientific papers
Autocleavage of O-isopropylidene protected O-phosphono- and O-thionophosphono esters of sugars
Postel, Denis,Ronco, Gino,Villa, Pierre
, p. 171 - 192 (2000)
Phosphorylation of D-glucose, D-galactose, D-fructose, glycerol and xylitol acetals with diethoxy-or diphenoxy(thiono)phosphoryl chloride gave the corresponding esters. A novel method of partially and fully deprotecting these compounds, which we have call
Substitution- and elimination-free phosphorylation of functionalized alcohols catalyzed by oxidomolybdenum tetrachloride
Liu, Cheng-Yuan,Pawar, Vijay D.,Kao, Jun-Qi,Chen, Chien-Tien
experimental part, p. 188 - 194 (2010/07/03)
Among 14 oxidometallic species examined for catalytic phosphorylation of the tested alcohols, oxidomolybdenum tetrachloride (MoOCl4) was found to be the most efficient with a negligible background reaction mediated by triethylamine (Et3N). The new catalytic protocol can be applied to the chemoselective phosphorylations of primary, secondary and tertiary alcohols as well as the substitution-free phosphorylations of allylic, propargylic, and benzylic alcohols. Functionalized alcohols bearing acetonide, tetrahydropyranyl ether, tert-butyldimethylsilyl ether, or ester group are also amenable to the new catalytic protocol. The most difficult scenarios involve substitution-free phosphorylations of 1-phenylethanol and 1-(2-naphthyl)ethanol which can be effected in 95 and 90% yields, respectively. ESI-MS, IR, 1H, and 31P NMR spectroscopic analyses of the reaction progress suggest the intermediacy of an alkoxyoxidomolybdenum trichloride-triethylamine adduct such as [(RO)Mo(O)Cl3-Et3N] to be responsible for the catalytic turnover.
Synthesis and Transformation of Sugar Phosphates
Bogusiak, J.,Szeja, W.
, p. 2181 - 2186 (2007/10/02)
Sugar diphenyl phosphates can be conveniently prepared by the treatment of monosaccharides with diphenylphosphorochloridate under phase-transfer conditions. Key words: synthesis, phosphorylation, sugar phosphates, catalytic two-phase system, thiosugars
USE OF O-THALLIUM(I) SALTS IN THE SYNTHESIS OF PHOSPHATE, SULFITE, AND RELATED ESTER DERIVATIVES OF CARBOHYDRATES
Granata, Alessandro,Perlin, Arthur S.
, p. 165 - 172 (2007/10/02)
O-Thallium(I) salts are shown to promote a variety of rapid, high-yield, substitution reactions at an anomeric, a primary, or a secondary position of carbohydrate derivatives.Synthesis are described of phosphates, phosphites, sulfites, and xanthic ester d
