Exploring hydrophobic diastereomeric 2,6-anhydro-glycoheptitols for their enzymatic polymerization with PEG: towards delivery applications

Abstract

Two sugar PEG-based amphiphilic copolymers have been synthesized by Novozym®-435-catalyzed greener solvent free transesterification reaction of diastereomeric 2,6-anhydro-glucoheptitol and 2,6-anhydro-mannoheptitol with PEG-1000 diethyl ester.

C-Glycopyranosyl aldehydes: emerging chiral synthons in organic synthesis

“…Khatri et al 115 recently synthesized a sugar–PEG copolymer starting from 2,6-anhydro heptitol 383a–b, which was obtained from β- C -glycopyranosyl aldehydes 4a–b by reduction with NaBH 4 followed by selective debenzylation of primary benzyl protection. The synthesized two diastereomeric sugar alcohol derived from d -glucose and d -mannose were employed for the synthesis of sugar PEG-based copolymers using PEG-1000 diethyl ester 552 and 553 in 80% and 76% yields, respectively ( Scheme 84 ).…”

“…Janes et al 113 and team explored the scope of organometallic C-glycosides containing chromium carbene and used b-C-glucopyranosyl aldehyde 4a for the synthesis. Glucopyranosyl aldehyde 4a on reaction with pentacarbonyl[(methoxy)- Khatri et al 115 recently synthesized a sugar-PEG copolymer starting from 2,6-anhydro heptitol 383a-b, which was obtained from b-C-glycopyranosyl aldehydes 4a-b by reduction with NaBH 4 followed by selective debenzylation of primary benzyl protection. The synthesized two diastereomeric sugar alcohol derived from Dglucose and D-mannose were employed for the synthesis of sugar PEG-based copolymers using PEG-1000 diethyl ester 552 and 553 in 80% and 76% yields, respectively (Scheme 84).…”