Synthesis of D-glucosyl esters, using unprotected β-D-glucose

Langmuir monolayers and Langmuir–Blodgett films of 1-acyl-1,2,4-triazoles

“…Due to the similarity in their structures this explanation for n-acyl-imidazoles we also assume for our substances. The denoted melting points of AcT-C2 and StT-C18 agree with literature data of 37-42°C and 71.5-75°C, respectively [53,54,60]. …”

“…ATs were synthesized via an acylation reaction of 1,2,4-triazole with carboxylic acid chlorides of different n-alkyl chain lengths as described elsewhere [52][53][54][55]. All chemicals used were purchased from Sigma-Aldrich (Germany), and used without further purification.…”

“…Table 1 presents the thermal properties of the ATs. The following substances are already known from literature: 1-acetyl- [56][57][58][59][60], 1-butyryl- [58][59][60][61], 1-caproyl- [59], 1-palmitoyl- [62,63], and 1-stearoyl-1,2,4-triazole [53,60,[62][63][64][65]. In contrast, 1-heptanoyl-, 1-octanoyl-, 1-nonanoyl-, 1-decanoyl-, 1-dodecanoyl-, and 1-myristoyl-1,2,4-triazole are described here for the first time.…”

One-Step Stereocontrolled Synthesis of α-Anomeric Carboxylic Acid Esters from Unprotected Glycosyl Donors: A Water-Soluble Aspirin Pro-Drug Analogue­

“…3 The aor b-ester can predominate depending on the solvent. In the first, 14 b-D-glucopyranose was treated with Nacyl 1,2,4-triazole or 1,3-imidazole in the presence of a catalytic amount of sodium hydride to give b-D-glucopyranosyl 1-esters. 4,5 Glycosyl 1-esters have been prepared as peracetates from the reaction of the corresponding glycosyl halides with silver 6 or cesium 7 carboxylates, or from the reaction of l-trichloroacetimidates with carboxylic acids.…”

“…A related method relies on the esterification of 2,3,4,6-tetra-O-benzyl D-glucopyranose with acyl chlorides in the presence of amine bases. 14 The regioselectivity was attributed to the comparatively higher acidity of the anomeric hydroxy group. 8 The selective cleavage of ester protecting groups while maintaining the anomeric ester in the products of the above reactions can be problematic because of anomerization and ester migration.…”