Issue 22, 1997
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

4,4′-Dimethoxytrityl and 4,4′,4″-trimethoxytrityl as protecting groups for amino functions; selectivity for primary amino groups and application in 15N-labelling

Alistair P. Henderson,   Jane Riseborough,   Christine Bleasdale,   William Clegg,   Mark R. J. Elsegood  and  Bernard T. Golding  

Abstract

4,4′-Dimethoxytrityl tetrafluoroborate (DMT+ BF4–) and 4,4′,4″-trimethoxytrityl tetrafluoroborate (TMT+ BF4–) are useful reagents for protecting primary and some secondary amines. Protected amines are obtained either by reaction of DMT+ BF4– or TMT+ BF4– with the amine or by alkylating DMT- or TMT-amine (available from DMT+ BF4– and TMT+ BF4– by treatment with ammonia). Alkylation of DMT- or TMT-amine stops after monoalkylation. Deprotection of the alkylated DMT- and TMT-amine is achieved by treatment with an acid of appropriate molarity (e.g. 0.1 M HCl in 1∶1 tetrahydrofuran–water for TMT-amines). The value of the methodology described is illustrated by a synthesis of (15NH2) adenosine. X-Ray molecular structures of one DMT and two TMT derivatives are reported.

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Article information

DOI
https://doi.org/10.1039/A703873I
Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1997, 3407-3414

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4,4′-Dimethoxytrityl and 4,4′,4″-trimethoxytrityl as protecting groups for amino functions; selectivity for primary amino groups and application in 15N-labelling

A. P. Henderson, J. Riseborough, C. Bleasdale, W. Clegg, M. R. J. Elsegood and B. T. Golding, J. Chem. Soc., Perkin Trans. 1, 1997, 3407 DOI: 10.1039/A703873I

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