deprotecting cpd for peptides
Also Known As:
TMS-TFMS; TMSOTf cpd; trimethylsilyltrifluoromethanesulfonate
relevant articles (0 outcomes,
Bio-Agent Context: Research Results
|2. ||Dehydration (Water Stress)
- "R-5-Methylcyclohex-2-enone 1 reacts successively with the phenyldimethylsilylzincate reagent and acetaldehyde to give with regiocontrol the aldols 7, dehydration of which creates the E-exocyclic double bond of the alpha,beta-unsaturated ketone 2. Conjugate addition of the ethylcuprate reagent to this compound takes place with high (96:4) selectivity in favour of the R stereoisomer 12, hydrolysis of which gives (2R,3R,5S,2'R)-2-(but-2'-yl)-3-dimethyl(phenyl)silyl-5-methylcyclohexanone 3. The oxime acetate of this ketone undergoes fragmentation in the presence of trimethylsilyl trifluoromethanesulfonate to give 3R,7R,5E-3,7-dimethylnon-5-enonitrile 4, in which an open-chain 1,5-stereochemical relationship is set up with a high level of stereocontrol.
Related Drugs and Biologics