𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Amphiphilic Carbohydrate-based Mesogens, IX. Mesogenic 4-O-Alkyl-D-glucoses via Methyl 4,6-O-Alkylidene-D-glucopyranosides

✍ Scribed by Dahlhoff, Wilhelm V. ;Riehl, Klaus ;Zugenmaier, Peter

Publisher
John Wiley and Sons
Year
1993
Tongue
English
Weight
454 KB
Volume
1993
Category
Article
ISSN
0947-3440

No coin nor oath required. For personal study only.

✦ Synopsis

Abstract

The 4,6‐O‐alkylidene derivatives (hexylidene–decylidene, 2a–e) are prepared by condensation of methyl α‐ or β‐D‐glucopyranoside 1 with alkanals in the presence of pyridinium tosylate. O‐diethylborylation of 2 gives 3 which are allowed to react firstly with bromodiethylborane and subsequently with sodium triethylhydroborate to yield methyl 4‐O‐alkyl‐D‐glucopyranosides 5 after deborylation. Acid hydrolysis of 5 gives mesogenic 4‐O‐alkyl‐D‐glucopyranoses 6a–e. The amphiphilic 6 exhibit the smectic A liquid crystalline phase on melting.

📜 SIMILAR VOLUMES

Amphiphilic carbohydrate-based mesogens,
Amphiphilic carbohydrate-based mesogens, V. Mesogenic 1-O-alkyl-D-glucitols from alkylD-glucopyranosides
✍ Dahlhoff, Wilhelm V. 📂 Article 📅 1990 🏛 John Wiley and Sons 🌐 English ⚖ 273 KB

## Abstract The endocyclic acetal bonds of alkyl D‐glucopyranosides (hexyl to decyl, 1a – e) are regioselectively hydroborated with ethyldiboranes(6) in the presence of 9‐methylsulfonyloxy‐9‐borabicyclo[3.3.1]nonane (MSBBN) after conversion to their 2,3,4,6‐tetra‐__O__‐diethylboryl derivatives 2a –

Amphiphilic carbohydrate-based mesogens,
Amphiphilic carbohydrate-based mesogens, VII. Synthesis of mesogenic 4- and 6-O-alkyl-D-glucitols
✍ Dahlhoff, Wilhelm V. 📂 Article 📅 1991 🏛 John Wiley and Sons 🌐 English ⚖ 488 KB

## Abstract Both the hemiacetal and acetal groups of 4,6‐__O__‐alkylidene‐α/β‐D‐glucopyranoses (hexylidene–decylidene, 1a–e) are quantitatively reduced by ethyldiboranes(6) in the presence of 9‐methylsulfonyloxy‐9‐borabicyclo[3.3.1]nonane (MSBBN) after conversion to their 1,2,3‐tri‐__O__‐diethylbor