61825-76-1Relevant articles and documents
Synthesis of haloconduritols from an endo-cycloadduct of furan and vinylene carbonate
Baran, Arif,Kazaz, Cavit,Se?en, Hasan,Sütbeyaz, Ya?ar
, p. 3643 - 3648 (2007/10/03)
A method for preparing haloconduritols having a conduritol-A construction is described. A mixture of endo- and exo-cycloadduct derivatives prepared from the Diels-Alder reaction of furan and vinylene carbonate was converted into diacetate derivatives by hydrolysis (K2CO3/MeOH) followed by acetylation (Ac2O/pyridine). Boron trihalide (BBr3 or BCl3)-assisted ring-opening of the endo-diacetate in CH2Cl2 at -78°C gave (1α,2α,3β,6β)-6-halogeno-4-cyclohexene-1,2,3-triol 1,2-diacetate from which the corresponding triacetate was prepared by acetylation (AcCl). trans-Esterification of the triacetate (MeOH/HCl) afforded (1α,2α,3β,6β)-6-halogeno-4-cyclohexene-1,2,3-triol (X=Br or Cl). BF3-Assisted ring-opening of the endo-diacetate in CH2Cl2 gave (1α,2α,3β,6β)-6-chloro-4-cyclohexene-1,2,3-triol 1,2-diacetate by means of halogen exchange.
Improved preparation of (±)-(1,3/2,4)-5-cyclohexene-1,2,3,4-tetrol [(±)-conduritol-B] and its reaction with hydrobromic and hydrochloric acid; synthesis and characterisation of some (±)-1-deoxy-1-halo- and (±)-1,4-dideoxy-1,4-dihalo-conduritols
Guo,Haines,Pyke,Pyke,Taylor
, p. 147 - 153 (2007/10/02)
An active-site directed, covalent inhibitor of α-glucosidases is the mixture of (±)-1-bromo (1,3/2,4)-5-cyclohexene-2,3,4-triol [(±)-1-bromo-1-deoxyconduritol F] (2), formed on treatment of (±)-conduritol-B (3) with hydrogen bromide and termed 'bromo cond
