180295-18-5Relevant academic research and scientific papers
Molecular sieves 5A as an acidic reagent: The discovery and applications
Asakura, Noriaki,Hirokane, Tsukasa,Hoshida, Hayato,Yamada, Hidetoshi
experimental part, p. 534 - 537 (2011/02/28)
The first use of molecular sieves (MS) 5A as an acidic reagent is described. We observed the acidic property during a dehydration reaction of 2-methyl-4-phenyl-3-butyn-2-ol. The acidity was sufficient to introduce ethoxyethyl and methoxyisopropyl protecting groups into alcohols. Additionally, the employment of MS 5A improved the synthesis of 1,2,4-orthoacetyl-α-d- glucopyranose at the intramolecular transorthoesterification step. In the other step of the synthesis, MS 4A was also applied to demonstrate that the manipulation of MS simplified the total operations.
A novel and efficient method for the synthesis of tetrahydropyranyl ethers catalyzed by Sc(OTf)3
Watahiki, Tsutomu,Kikumoto, Hisashi,Matsuzaki, Masaya,Suzuki, Takeshi,Oriyama, Takeshi
, p. 367 - 368 (2007/10/03)
Reaction of alcohols with dihydropyran in the presence of a catalytic amount of Sc(OTf)3 provides efficiently the corresponding tetrahydropyranyl ethers. After the reaction, the catalyst can be recovered quantitatively from the aqueous media and reused without loss of the activity.
A novel and chemoselective transformation of alcohol silyl ethers into the corresponding tetrahydropyranyl ethers
Suzuki,Oriyama
, p. 555 - 558 (2007/10/03)
Direct conversion of alcohol silyl ethers into the corresponding tetrahydropyranyl (THP) ethers can be easily performed by reaction with THP acetate under the influence of a catalytic amount of tert-butyldimethylsilyl trifluoromethanesulfonate (TB-SOTf). Aliphatic TBS ether can be selectively transformed into the corresponding THP ether in the presence of phenolic TBS ether.
