4176-55-0Relevant articles and documents
Synthesis and biological evaluation of deoxy salacinols, the role of polar substituents in the side chain on the α-glucosidase inhibitory activity
Muraoka, Osamu,Yoshikai, Kazuya,Takahashi, Hideo,Minematsu, Toshie,Lu, Guangxin,Tanabe, Genzoh,Wang, Tao,Matsuda, Hisashi,Yoshikawa, Masayuki
, p. 500 - 509 (2007/10/03)
Three analogs (5, 6, and 7) lacking polar substituents in the side chain of a naturally occurring α-glucosidase inhibitor, salacinol (1a), were synthesized by the coupling reaction of a thiosugar, 1,4-dideoxy-1,4-epithio-d- arabinitol (3), with cyclic sulfates (8, 9, and 10), and their α-glucosidase inhibitory activities were examined. All these simpler analogs (5, 6, and 7) showed less inhibitory activity compared to 1a, and proved the importance of cooperative role of the polar substituents for the α-glucosidase inhibitory activity. A practical synthetic route to 3 starting from d-xylose is also described.
Reaction of diethylaminosulfur trifluoride with diols
Shellhamer, Dale F.,Anstine, D. Timothy,Gallego, Kelly M.,Ganesh, Brian R.,Hanson, Aaron A.,et al.
, p. 861 - 866 (2007/10/02)
Diethylaminosulfur trifluoride (DAST) reacts with dialcohols to give difluorides, sulfite esters or cyclic ethers depending on the number of carbons separating the two alcohol groups.Vicinal and 1,3-diols give large amounts of sulfite ester products while butane-1,4-diol gives almost exclusively the cyclic ether tetrahydrofuran.Terminal dialcohols longer than four carbons give primarily difluoride products.Semiempirical calculations indicate a preference for cyclic intermediates when four or less carbons separate the two alcohol moieties.These cyclic intermediates lead directly to the cyclic ethers and sulfite ester products.
ELECTROCHEMICAL REDUCTION OF CYCLIC AND ACYCLIC SULFATES.
Nonaka,Kihara,Fuchigami,Baizer
, p. 3160 - 3166 (2007/10/02)
It was confirmed that cyclic and acyclic sulfates of diols and monoalcohols could be reduced at cathodes in nonaqueous solvents. The reduction products were greatly affected by the molecular structures of the sulfates. The reduction of the cyclic sulfates of 1,2-diols yielded the corresponding alkenes and disulfate dianions of the parent diols in high yields and current efficiencies were based on one-electron reduction. On the other hand, the cyclic sulfates of 1,3- and 1,4-diols were also reduced by one-electron transfer under similar conditions, but the cycloalkanes expected were not formed and the products were cyclic ethers along with acyclic alkane or unsaturated alcohol. The reduction of the cyclic sulfate of hydrated formaldehyde, which is regarded as a 1,1-diol, did not give any identified products except for a small amount of methane.