Regioselective Copolymerization of Acryl Sucrose Monomers

Abstract

1',2,3,3',4,4',6-Hepta-O-benzyl-sucrose has been prepared and selectively 6'-O-esterified with small alpha,beta-unsaturated acid derivatives. New chiral copolymers containing sucrose have been synthesized by radical polymerization, and some of their physical properties have been determined.

Straight and Branched Sucrose Monoamide Derivatives as New Surfactants

“…NMR spectra were recorded on Jeol and Bruker spectrometers at 400 MHz for 1 H and 100 MHz for 13 C, respectively. Assignments of 13 C-signals are based on HMQC spectra 4,5 . High-resolution mass spectra were recorded on an LC-MS system, applying MeOH/water eluents.…”

“…The solution was cooled to room temperature, diluted with water and extracted with dichloromethane. The organic layer was washed with water, saturated NaHCO 3 solution and water, dried over MgSO 4 and concentrated under reduced pressure. After acetylation with acetic anhydride (2.0 eq.)…”

Sucrose chemistry: Fast and Efficient Microwave-assisted Protocols for the Generation of Sucrose-Containing Monomer Libraries

“…The advantage of using trityl chloride over TBDPSCl is that it is a relatively cheap reagent, but unfortunately, it is not selective for mono-protection. Thus, the first step in many protection-deprotection sequences to obtain valuable monofunctionalized compounds often consists of a regioselective silylation of the 6'-hydroxyl group of the sucrose (Barros et al, 2000a;Barros et al, 2004b;Crucho et al, 2008) using 1.1 equiv. of tert-butyldiphenylchlorosilane (TBDPSCl) in dry pyridine.…”

“…of tert-butyldiphenylchlorosilane (TBDPSCl) in dry pyridine. The methods have been described for sucrose first by Karl et al, (Karl et al, 1982) to obtain a 49 % yield, and later (Barros et al, 2004b) optimized to 85 % by closely following the reaction by TLC and stopping it when di-O-TBDPS sucrose first appeared as a less polar product. A similar strategy has been applied to obtain 6,6'-di-O-TBDPS-sucrose, where 2.2 eq TBDPSCl were used (Karl et al, 1982).…”

“…The monomers have been prepared either by multistep synthesis, leading to defined compounds and subsequently a well-defined polymerization processes (Fig. 6,7), (Barros et al, 2004b;Barros and Petrova, 2009;Barros et al, 2007;Barros and Sineriz, 2002;Crucho et al, 2008), or by direct functionalization of unprotected sucrose, leading to mixtures of isomers and therefore to more complex polymers (Barros et al, 2010b). A number of monomers has been synthesized from sucrose during the last decades, as presented in Fig.…”