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Mild reagent for the silylation (see Appendix 4) of alcohols, including carbohydrates; cf N,O-Bis(trimethylsilyl)acetamide, L00183. O-Silylation in the presence of TBAB (0.02 equiv.) occurs under very mild conditions: Tetrahedron Lett., 35, 8409 (1994)./n
n-BuLi forms the dilithio-derivative which can act as a soluble enolate equivalent of acetamide, reacting with electrophiles at carbon: J. Org. Chem., 49, 2015 (1984)./n
Used in combination with triflic anhydride for N-glycosylation of sugars: J. Am. Chem. Soc., 111, 6881 (1989)./n
Hazard Statements: H315-H319-H335
Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P261-P280a-P305+P351+P338-P304+P340-P405-P501a
Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.