76358-57-1Relevant academic research and scientific papers
Synthesis of conformationally locked carbocyclic nucleosides built on a thiabicyclo[3.1.0]hexane system as a pseudosugar surrogate
Elhalem, Eleonora,Comin, Maria J.,Rodriguez, Juan B.
, p. 4473 - 4482 (2006)
The synthesis of prototype models of purine and pyrimidine carbanucleosides built on a 6-thiabicyclo[3.1.0]hexane system as pseudosugar moiety has been investigated. These pyrimidine carbanucleosides proved to be very stable compounds, in contrast to the parent epoxy analogs, which experienced epoxide ring-opening due to intramolecular enol base attack. In addition, as the synthesis of a thiirane moiety fused to a five-membered ring is not a trivial synthetic task, validation and optimization of the existing methods for episulfide preparation were required to access the committed synthetic precursor of the title compounds: (±)-(1RS,2RS,5SR)-6-thiabicyclo[3.1.0]hexan-2- ol, compound 28. Wiley-VCH Verlag GmbH & Co. KGaA, 2006.
Carbon-nitrogen bond formation between allyl silyl ether and hydrazide promoted by mercuric triflate catalyst
Yamamoto, Hirofumi,Yamasaki, Naoto,Yoshidome, Shingo,Sasaki, Ikuo,Namba, Kosuke,Imagawa, Hiroshi,Nishizawa, Mugio
supporting information; experimental part, p. 1069 - 1073 (2012/06/04)
An efficient method for carbon-nitrogen bond formation between ally silyl ethers and N,N-acyltosylhydrazine was developed under very mild conditions using 2 mol% of mercuric triflate [Hg(OTf) as a catalyst. This method does not require the use of any ligand system or supplementary additives and is applicable to the preparation of various N-allylhydrazides with good to excellent yields. Georg Thieme Verlag Stuttgart · New York.
Silyl Halides from (Phenylseleno)silanes. Reaction with Oxiranes and Alcohols To Give Hydrolytically Stable Silyl Ethers.
Detty, Michael R.,Seidler, Mark D.
, p. 1283 - 1292 (2007/10/02)
The preparation of (phenylseleno)silanes and their reactions with halogens (Cl2, Br2, I2) to give silyl halides and diphenyl diselenide are described.Highly hindered tert-butyldimethyl and tert-butyl diphenylsilyl halides were easily prepared.The reaction of silyl bromides and iodides with oxiranes followed by diazabicyclononane treatment gave allylic alcohol silyl ethers.Tertiary alcohols reacted rapidly with silyliodides to give hydrolytically stable silyl ethers.Treatment of the silyl ethers with tetra-n-butylammonium fluoride gave the free alcohols withoutrearrangement or isomerization.
