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Amphiphilic carbohydrate-based mesogens, V. Mesogenic 1-O-alkyl-D-glucitols from alkylD-glucopyranosides

✍ Scribed by Dahlhoff, Wilhelm V.

Publisher
John Wiley and Sons
Year
1990
Tongue
English
Weight
273 KB
Volume
1990
Category
Article
ISSN
0947-3440

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✦ Synopsis

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 – e. Subsequent deboronations give the mesogenic 1‐O‐alkyl‐D‐glucitols 3a – e.

📜 SIMILAR VOLUMES

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

Amphiphilic Carbohydrate-based Mesogens,
Amphiphilic Carbohydrate-based Mesogens, IX. Mesogenic 4-O-Alkyl-D-glucoses via Methyl 4,6-O-Alkylidene-D-glucopyranosides
✍ Dahlhoff, Wilhelm V. ;Riehl, Klaus ;Zugenmaier, Peter 📂 Article 📅 1993 🏛 John Wiley and Sons 🌐 English ⚖ 454 KB

## 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

Amphiphilic carbohydrate-based mesogens,
Amphiphilic carbohydrate-based mesogens, VI. Synthesis of a series of alkyl 1-thio-D-glucopyranosides and their regioselective reductions to 1-alkylthio-1-deoxy-D-glucitols
✍ Dahlhoff, Wilhelm V. 📂 Article 📅 1990 🏛 John Wiley and Sons 🌐 English ⚖ 328 KB

## Abstract Alkyl 1‐thio‐α,β‐D‐glucopyranosides (hexyl to decyl, 1a–e) are prepared by reaction of penta‐__O__‐acetyl‐β‐D‐glucopyranose with the respective thiols in the presence of diethyl ether — trifluoroborane, followed by deacetylation. 1a–e are converted into their tetra‐__O__‐diethylboryl de