2,4,6-Triisopropylbenzene-sulfonyl azide

Chemical Properties

White wet solid

Uses

Reagent for:• ;Stereoselective diversity-oriented synthesis of functionalized saccharides1• ;Meyer′s lactamization2Reagent for synthesis of:• ;Antidote to anthrax lethal factor intoxication3• ;Bacterial RNA polymerase inhibitor4• ;Bicyclic extended dipeptide surrogates5• ;Single enantiomers of mycobacterial keomycolic acids6

Uses

2,4,6-Triisopropylbenzenesulfonyl azide is used as a reagent for diazo transfer to ketones, e.g. under phase-transfer conditions, giving better yields of sterically-hindered -diazo ketones than other methods. It is also used for azide transfer to potassium enolates (KHMDS) to form the -azido derivatives.

Preparation

2,4,6-Triisopropylbenzene-sulfonyl azide is readily prepared by treatment of the commercially available triisopropylbenzenesulfonyl chloride (trisyl chloride) with sodium azide.^[1]

References

1. Leffler, J. E.; Tsuno, Y. JOC 1962, 28, 902.