[13795-24-9] · C14H11NO5 · Benzyl 4-Nitrophenyl Carbonate · (MW 273.24)
(reagent for protection of tryptophan nucleus1)
Physical Data: mp 78-80 °C.
Solubility: sol ether, methanol, chloroform.
Form Supplied in: fibrous powder.
Protection of the indole ring on a tryptophan residue, as an acid-stable Cbz derivative, was required for the synthesis of a tetrapeptide target molecule. Thus reaction of a Boc-protected dipeptide fragment with the reagent (1) and Potassium Fluoride solubilized with 18-Crown-6 provided the Cbz-protected derivative (eq 1). The naked fluoride ion serves as the base to abstract a proton from the indole ring.
Eric D. Edstrom
Utah State University, Logan, UT, USA