Protection bromoethyl esters

In a synthesis of the L-serine derivative 133, Kunz and Buchholz100 treated N-(benzyloxycarbonyl)-L-serine 2-bromoethyl ester (135) with tetra-O-benzoyl-a-D-glucopyranosyl bromide (136) protection of the... 

The conditions required for the Michaelis-Becker reaction are generally mild, from the point of view of temperature, in contrast to the higher temperatures normally required in the Michaelis-Arbuzov procedure, and this important feature allows its use in the formation of peptides containing terminal (aminoalkyl)phosphonic ester groups. Even so, the alkalinity of the media in which the former reactions take place may result in secondary reactions when A-protection in a substrate is afforded by a phosphoryl substituent, as in a dialkyl A-(2-bromoethyl)phosphoramidate, loss of HBr may occur with the formation of dialkyl A-ethenylphosphoramidate and l-(dialkoxyphosphinyl)aziridine ... 

Protection of carboxyl groups. 2-Bromoethyl and 2-chloroethyl esters of carboxylic acids are cleaved in 90-99% yield by NaHSe in C2H5OH (20°, 1 hour). ... 

Cleavage of Haloethyl Derived Protecting Groups. Samarium diiode is a mild and effective reagent for the deprotection of 2-bromoethyl and 2-iodoethyl esters and (2,2,2-trichloroethoxy) methoxy ethers. ... 

---