249284-22-8Relevant academic research and scientific papers
A Highly Efficient and Chemoselective Synthetic Protocol for Tetrahydropyranylation/Depyranylation of Alcohols and Phenols
Khan, Abu T.,Mondal, Ejabul,Borah, Ballav M.,Ghosh, Subrata
, p. 4113 - 4117 (2003)
Various alcohols and phenols can be converted efficiently to the corresponding tetrahydropyranyl (THP) ethers in good yields using catalytic amounts of bromodimethylsulfonium bromide (0.005-0.02 equivalent) at room temperature. On the other hand, various THP ethers can also be deprotected to the parent alcoholic or phenolic compounds in CH2Cl2/ MeOH (5:2) by employing 0.05 equivalent of the same catalyst. Some of the major advantages of this procedure are its mild conditions, that it is highly selective and efficient, high yielding, and cost-effective, that it needs no solvent and is compatible with the presence of other protecting groups. Furthermore, no brominations occur at a double or triple bond, at an allylic position or even at an aromatic ring. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
Tetrahydropyranylation and depyranylation of alcohols catalyzed by aqueous zinc tetrafluoroborate
Islam, Samimul,Majee, Adinath,Khan
, p. 1789 - 1793 (2007/10/03)
Aqueous solution of zinc tetrafluoroborate as an effective catalyst for tetrahydropyranylation and depyranylation of alcohols has been described. Copyright Taylor & Francis, Inc.
A highly efficient synthetic protocol for tetrahydropyranylation/ depyranylation of alcohols and phenols
Khan, Abu T.,Ghosh, Subrata,Choudhury, Lokman H.
, p. 4891 - 4896 (2007/10/03)
Bismuth(III) nitrate pentahydrate [Bi(NO3)3· 5H2O] is found to be an effective catalyst for both tetrahydropyranylation and depyranylation of alcohols and phenols. Some of the major advantages of this protocol are: non-aqueous workup, good yields, the involvement of a less-expensive and nontoxic catalyst, and compatibility in the presence of a large number of other protecting groups. Notably, isopropylidene, benzylidene, and thioacetal groups are also unaffected under the experimental conditions. Remarkably, a selective mono-protection of diols and primary alcohols can be achieved chemoselectively by employing the same catalyst. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.
Iodine-Catalyzed Mild and Efficient Tetrahydropyranylation/Depyranylation of Alcohols
Kumar, H. M. Sampath,Reddy, B. V. Subba,Reddy, E. Jagan,Yadav, J. S.
, p. 857 - 858 (2007/10/03)
Alcohols and phenols are tetrahydropyranylated rapidly in high yields in the presence of catalytic amount of iodine at room temperature. Depyranylation is effected readily by refluxing with iodine in methanol for few hours.
