3,5-Dimethoxybenzyl 4-Nitrophenyl Carbonate

[6453-62-9]  · C16H15NO7  · 3,5-Dimethoxybenzyl 4-Nitrophenyl Carbonate  · (MW 333.30)

(amino-protecting group used in peptide synthesis1)

Physical Data: mp 114-15 °C.

Solubility: sol chloroform, THF.

Preparative Method: by reduction of 3,5-dimethoxybenzoic acid with Lithium Aluminum Hydride and then acylation of the resulting 3,5-dimethoxybenzyl alcohol with 4-nitrophenyl chloroformate.1

N-Protection of Amino Acids.

Reaction of amino acids with the reagent (1) in aqueous THF in the presence of Sodium Hydroxide affords 3,5-dimethoxybenzyloxycarbonyl derivatives in 55-76% yields (eq 1).1 This protecting group can be cleaved by irradiation with a high-pressure mercury lamp for 1.5 h in aqueous dioxane (42-85% yields). The advantage is provided in that acidic, basic, or reductive reaction conditions can be avoided.

1. Chamberlin, J. W. JOC 1966, 31, 1658.

Eric D. Edstrom

Utah State University, Logan, UT, USA

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