Synthesis of a sucrose-based macrocycle with unsymmetrical monosaccharides "arms"

An efficient methodology for the selective substitution of both terminal positions (C6 and C6’) in 1’,2,3,3’,4,4’-hexa-O-benzylsucrose with different unsaturated monosaccharide units is presented. Such a highly functionalized intermediate was cyclized under RCM conditions to afford a macrocyclic derivative containing a 31-membered ring in 26% yield

Short Synthesis of Diamide-Linked Sucrose Macrocycles

A convenient route to macrocyclic diamide-linked macrocyclic derivatives with a sucrose scaffold is presented. Reaction of sucrose based amines (<i>o</i>- and <i>m</i>-) with acid dichlorides afforded the monomeric macrocycles in excellent yields, while reaction of the <i>p</i>-amines also provided dimeric products

An efficient synthesis of a C12-higher sugar aminoalditol

The C12-aminoalditol H2NCH2–(CHOBn)10–CH2OH was prepared from two simple monosaccharide building blocks. The synthesis was realized by a regioselective introduction of the azide group and subsequent protection–deprotection transformations. The chemical reactivity of the aminoalditol was tested in the reductive amination reaction with a selectively protected sucrose monoaldehyde

Short Synthesis of Diamide-Linked Sucrose Macrocycles

A convenient route to macrocyclic diamide-linked macrocyclic derivatives with a sucrose scaffold is presented. Reaction of sucrose based amines (<i>o</i>- and <i>m</i>-) with acid dichlorides afforded the monomeric macrocycles in excellent yields, while reaction of the <i>p</i>-amines also provided dimeric products

Synthesis of Highly Oxygenated Bicyclic Carbasugars. Remarkable Difference in the Reactivity of the d-gluco and d-xylo- Derived Trienes

2,3,4-Tri-O-benzyl-D-xylopyranose was used as a starting material in the preparation of the corresponding triene, which underwent smooth cyclization to a polyhydroxylated hydrindane, as a single diastereoisomer. The analogous triene prepared from D-glucose did not undergo any cyclization even under high pressure

<i>N</i>,<i>O π</i>-Conjugated 4‑Substituted 1,3-Thiazole BF₂ Complexes: Synthesis and Photophysical Properties

A series of 1,3-thiazole-based organoboron complexes has been designed and synthesized by acylation of 2-amino 4-subsituted 1,3-thiazoles with (4-dimethylamino)­benzoyl chloride and the subsequent BF₂ complexation reaction. The influence of substituents in position 4 of the thiazole ring on photophysical properties of the complexes has been investigated. Synthesized thiazolo­[3,2-<i>c</i>]­[1,3,5,2]­oxadiazaborinines mainly showed intensive fluorescence in solutions. Complex with a 4,5-unsubstituted thiazole unit demonstrated an aggregation induced emission (AIE) effect and a very high fluorescent quantum yield (94%) in the solid state because of the inhibition of π–π/π–<i>n</i> interactions in the molecular packing