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Reagent for conversion of cis-1,2-diols, including nucleosides, via cyclic dioxolanone intermediates, into trans-chloroalkyl acetates. The reaction is selective for the 2'-OH of uridine derivatives and converts pyrimidine nucleosides to their anhydro forms: J. Am. Chem. Soc., 95, 4016 (1973). Application to synthesis of deoxy-sugars, by dechlorination with Bu3SnH: J. Chem. Soc., Chem. Commun., 677 (1978)./n
Reaction of the chloroalkyl acetate (from a cis-glycol) with azide ion provides a route to the cis-amino alcohol: Tetrahedron Lett., 37, 2529 (1996). Compare O-Acetylsalicyloyl chloride, L00919./n
Hazard Statements: H227-H314-H318-H335
Combustible liquid. Causes severe skin burns and eye damage. Causes serious eye damage. May cause respiratory irritation.
Precautionary Statements: P210u-P260u-P303+P361+P353-P305+P351+P338-P405-P501a
Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Do not breathe dusts or mists. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.