4485-40-9Relevant academic research and scientific papers
The X-ray crystal structure, conformation and preparation of anti-3,3,6,6-tetramethylthiepane-4,5-diol: Stereochemistry of reduction of a heterocyclic α-hydroxy ketone
Feeder, Neil,Ginnelly, Michael J.,Jones, Ray V. H.,O'Sullivan, Susan,Warren, Stuart,Wyatt, Paul
, p. 3479 - 3483 (1997)
The X-ray crystal structure and conformation of the anti title diol is described together with stereoselective syntheses of syn- and anti-diols from a readily available acyloin. Some control of the stereoselective reduction of α-hydroxy ketones by chelating and non-chelating reducing agents is possible. Copyright 1997 by the Royal Society of Chemistry.
TMTHSI, a superior 7-membered ring alkyne containing reagent for strain-promoted azide-alkyne cycloaddition reactions
Hadavi, Darya,Honing, Maarten,Ippel, Hans,Liskamp, Rob M. J.,Meulemans, Tommi,Rijcken, Cristianne J. F.,Timmers, Matt,Veldhuis, Harald,Weterings, Jimmy
, p. 9011 - 9016 (2020/10/15)
We describe the development of TMTH-SulfoxImine (TMTHSI) as a superior click reagent. This reagent combines a great reactivity, with small size and low hydrophobicity and compares outstandingly with existing click reagents. TMTHSI can be conveniently func
Thiacycloalkynes for copper-free click chemistry
De Almeida, Gabriela,Sletten, Ellen M.,Nakamura, Hitomi,Palaniappan, Krishnan K.,Bertozzi, Carolyn R.
, p. 2443 - 2447 (2012/04/23)
The heteroatom helps! The introduction of an endocyclic sulfur atom enables fine-tuning of the reactivity and stability of thiacycloalkynes for copper-free click chemistry. The stabilizing effect of the endocyclic sulfur atom allows the use of highly activated seven-membered rings as reagents for bioorthogonal copper-free click chemistry. Copyright
New tetramethylthiepinium (TMTI) for copper-free click chemistry
King, Mathias,Baati, Rachid,Wagner, Alain
, p. 9308 - 9309 (2012/09/25)
A new derivative of the strained 3,3,6,6-tetramethylthiacycloheptyne (TMTH) bearing a functional handle is reported. Following an optimized synthesis, the handle was introduced by mild alkylation of the sulphur atom. The resulting functionalized strained 4,5-didehydro-3,3,6,6-tetramethyl-2,3,6,7- tetrahydrothiepinium (TMTI) proved to be stable and underwent extremely fast [3+2] cycloaddition reaction with benzyl azide in both organic and aqueous solvents. The reaction was equally efficient in cell lysate and serum and therefore opens interesting prospects for chemical-biology applications.
