Mild One‐Step Synthesis of 4, 6‐Benzylideneglycopyranosides from Aromatic Aldehydes and Gelation Abilities of the Glucose Derivatives. Issue 29 (6th August 2015)

• Record Type: Journal Article
• Authors: Ono, Fumiyasu; Hirata, Osamu; Ichimaru, Keiko; Saruhashi, Koichiro; Watanabe, Hisayuki; Shinkai, Seiji
• Is Part Of: European journal of organic chemistry. Issue 29(2015)
• Page Start: 6439
• Page End: 6447
• Publication Date: 2015-08-06
• Subjects: Carbohydrates -- Protecting groups -- Self‐assembly -- Gels -- Nanostructures; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201500658
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: We report herein an efficient one‐step synthesis of 4, 6‐benzylidene glycoside derivatives from aromatic aldehydes bearing electron‐donating or ‐withdrawing groups as well as polymerisable monomer groups. Glucose, mannose and galactose derivatives could also be used successfully. Several of the glucose derivatives thus obtained acted as gelators for various solvents, including water. 4‐( n ‐Butoxybenzylidene)glucose derivative3a produced both a clear squalane gel and a hydrogel at 0.1 wt.‐%. Furthermore, 3‐( n ‐butoxybenzylidene)glucose derivative3i produced a clear organogel and an opaque hydrogel. The critical gelation concentration (CGC) of3i in squalane was determined to be 0.02 wt.‐%, which is one of the lowest CGC values reported so far. The organogels, hydrogels and aqueous solution gels produced from3a and3d exhibited thixotropy. The strength and thixotropy of the organo‐ and hydrogel produced from3a were estimated by a rheometer. The gel morphologies were observed by field‐emission and wet‐scanning electron microscopy, and the self‐assembly modes were analysed by XRD. We have concluded that super‐gelators can be created by this method. Abstract : An efficient one‐step synthesis of 4, 6‐benzylidene glycosides from aromatic aldehydes under mild conditions has been achieved. Some of the glucose derivatives synthesised by this method produced clear organo‐ and hydrogels with thixotropic properties. The critical gelation concentrations of the gels were below 0.1 wt.‐%.