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Preparation, Characterisation, and Structure of N-Methylated Derivatives of 1,3,5-Triamino-1,3,5-trideoxy-cis-inositol: Polyalcohols with Unusual Acidity

✍ Scribed by Kaspar Hegetschweiler; Isidor Erni; Walter Schneider; Helmut Schmalle

Publisher
John Wiley and Sons
Year
1990
Tongue
German
Weight
503 KB
Volume
73
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

1,3,5‐Trideoxy‐1,3,5‐tris(dimethylamino)‐cis‐inositol (TDCI) and 1,3,5‐trideoxy‐1,3,5‐tris(trimethylammonio)‐cis‐inositol (TTCI) were prepared by methylation of 1,3,5‐triamino‐1,3,5‐trideoxy‐cis‐inositol (TACI). The ability of TDCI to form both intermolecular and intramolecular H‐bonds, as demonstrated by X‐ray diffraction, is probably responsible for the good solubility of TDCI in almost every common solvent. TTCI was found to be a polyol of unusual high acidity (p__K__~1~ = 8.14 ± 0.02, p__K__~2~ = 13.0 ± 0.2). This phenomenon could be explained by electrostatic interactions between the charged substituents of the cyclohexane residue.

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1,3,5-Triamino-1,3,5-trideoxy-cis-inosit
1,3,5-Triamino-1,3,5-trideoxy-cis-inositol, a New Ligand with a Remarkable Versatility for Metal Ions. Part 2. Safe and efficient ligand preparation and structure of the free ligand and the CoIII complex
✍ Michele Ghisletta; Kaspar Hegetschweiler; Hans-Peter Jalett; Tobias Gerfin; Volk 📂 Article 📅 1992 🏛 John Wiley and Sons 🌐 German ⚖ 547 KB

## Abstract A new, convenient, and safe route to 1,3,5‐triamino‐1,3,5‐trideoxy‐__cis__‐inositol (taci) was investigated by hydrogenation of azo‐coupled derivatives of phloroglucinol. In the presence of acetic anhydride, the reduction of trisphenylazophloroglucinol (H~2~/Pd(5%) on C) resulted in the