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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 45, 2015 - Issue 20
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Original Articles

Synthesis of Some Selectively N-Protected (1S,2S)-p-Nitrophenylserinol–Based Diamino-1,3-dioxanes and Tripodands

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Pages 2319-2330 | Received 23 May 2015, Published online: 11 Sep 2015
 

Abstract

The unconventional methodology for the non-epimerizable cycloacetalization of optically active (1S,2S)-2-amino-1-(4-nitrophenyl)propane-1,3-diol (p-nitrophenylserinol) (condensed H2SO4 96% as solvent and catalyst, i.e., sulfuric transacetalization) producing (2R,4S,5S) diamino-1,3-dioxanes was enlarged by the use of N-protected forms of 2,2-dimethoxyethylamine (DMEA, aminoacetaldehyde dimethylacetal). Conversely, N-protected derivatives of p-nitrophenylserinol were successfully cyclocondensed with DMEA in the same sulfuric conditions. N-Functionalization of DMEA upon treatment with trimesic acid trichloride and cyanuric chloride yielded the corresponding triple amide and melamine, respectively. Their adapted sulfuric transacetalization in triplicate in reaction with arylserinols (aryl: phenyl, p-nitrophenyl) afforded a new series of optically active tripodands.

GRAPHICAL ABSTRACT

Supporting Information

(Typical) procedures for preparations of compounds 1a, 1b, 1c, 3b, 4b, 4c, 1d, and 1e; full analytical data of compounds 1a, 1b, 1c, 2b, 3b, 4b, 4c, 2a, 5a, 5b, 1d, 1e, 6e, and 7d; 1H and 13C NMR spectra of compounds 1a, 1b, 1c, 2b, 4b, 4c, 3b, 2a, 5a, 5b, 1d, 1e, 6d, 6e, and 7d; and MS of compounds 6d, 6e, and 7d for this article can be accessed on the publisher’s website.

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