Benzyl 4-Nitrophenyl Carbonate

[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.

Tryptophan Protection.1

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.

Related Reagents.

Benzyl Chloroformate.

1. Chorev, M.; Klausner, Y. S. CC 1976, 596.

Eric D. Edstrom

Utah State University, Logan, UT, USA

Copyright 1995-2000 by John Wiley & Sons, Ltd. All rights reserved.