Troc-OSu

Published on 09/11/2011

Reported applications:

Introduction of 9-fluorenylmethyloxycarbonyl, trichloroethoxycarbonyl, and benzyloxycarbonyl amine protecting groups into O-unprotected hydroxylamino acids using succinimidyl carbonates; Anelka Paquet; Can. J. Chem.; 1982; 60: 976.

Widely Applicable Deprotection Method of 2,2,2-Trichloroethoxycarbonyl (Troc) Group Using Tetrabutylammonium Fluoride; Cheng-yuan Huanga; Ning Wanga; Katsumasa Fujikia; Yuji Otsukaa; Masao Akamatsua; Yukari Fujimotoa; Koichi Fukasea; Journal of Carbohydrate Chemistry 2010; 29(6): 289 – 298.

Product of the month May:

Troc-OSu – a versatile Amine Protecting Agent

A convenient and versatile Protecting Group for Amines

Troc-OSu

Synonyms:

Formula:
Molecular Weight:
CAS:

Troc-NHS, Succinimidyl 2,2,2-trichlororethyl carbonate
N-(2,2,2-Trichloroethoxycarbonyloxy)succinimide
C₇H₆Cl₃NO₅
290,49 g/mole
66065-85-8

Code	RL-1205
25g:	EUR 125	US$ 193.75
100g:	EUR 300	US$ 465

Prices are in EUR/USD, net, exw Germany, shipping not include

Troc-OSu is a convenient alternative to the widely used Troc-Cl. Troc-Cl finds broad applications in carbohydrate synthesis and total synthesis of natural products. However, it is toxic and skin irritant. It is a severe eye irritant and lacrimetric.

Troc-OSu is a stable, crystalline product and does not have toxic or any irritant properties. It is less reactive, therefore, has higher selectivity and creates less side reactions and impurities. Troc belongs to the orthogonal set of protecting groups, cleaved by beta-elimination. It can be removed in the presence of Trifluoroacetamides, Aloc, Boc, Fmoc, and Cbz groups. It easily survives the conditions for removing Boc and Fmoc, however is unstable towards hydrogenolysis.

Deprotection can be carried out by treatment with Tetrabutylammonium fluoride (TBAF) under very mild conditions or by hydrogenolysis with Zn in HCl or AcOH.

Reported applications:

Abstract:

The N-Troc (2,2,2-trichloroethoxycarbonyl) groups in glucosamine and muramic acid derivatives were removed by treatment with tetrabutylammonium fluoride (TBAF) under mild conditions. The use of Troc protection for the amino group in aminosugars such as glucosamine is increasing the importance for selective and efficient glycosylation, and the cleavage method described here will expand the available opportunities for using the Troc group in the preparation of a variety of glycans. This cleavage is especially advantageous for compounds that are labile or may be decomposed under acidic conditions, strong basic conditions, or reductive conditions.

Mild Approach to the Deprotection of Troc from Protected Amines Using Mischmetal and TMSCl; Eerold Vellemea; Vladimir Stepanova; Uno Meorga; Synthetic Communications: An International Journal for Rapid Communication of Synthetic Organic Chemistry; 2010; 40(22): 3397 – 3404.

Selective conversion of N-trichloroethoxycarbonyl (Troc) groups into N-acetyl groups in the presence of N-tert-butoxycarbonyl (Boc) protecting groups, X. Zhu and R. R. Schmidt, Synthesis; 2003; 8: 1262-1266.

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