Levoglucosan and levoglucosenone as bio-based platforms for polymer synthesis

Abstract

Levoglucosan (LGA) and levoglucosenone (LGO) are compounds readily obtained from biomass via pyrolysis of cellulose and represent a renewable pathway to prepare monomeric building blocks to synthesise polymeric materials. LGO...

Catalytic Transformation of Carbohydrates into Renewable Organic Chemicals by Revering the Principles of Green Chemistry

“… Mineral acids like H 2 SO 4 and H 3 PO 4 were used as catalyst in earlier studies, which is now being replaced with heterogeneous acid catalysts (e.g., zeolites) . LGO can be used as a chiral moiety to synthesize chiral bioactive molecules, biobased polymers, and develop chiral ligands for asymmetric synthesis. − Hydrogenation of the olefinic group in LGO leads to cyrene, which is a promising biorenewable solvent . However, the production of LGO must be improved (e.g., yield, scalability) further to improve the availability and decrease the cost of cyrene.…”

Skeletal rearrangement of 6,8-dioxabicyclo[3.2.1]octan-4-ols promoted by thionyl chloride or Appel conditions

“…Lab scale synthesis of this chiral material can be accomplished in a single step without special glassware [3], while large scale production of the reduction product cyrene (2) allows for its use as a chiral solvent [4]. This product is emerging as a promising platform chemical for the construction of chiral small molecules for pharmaceuticals [5][6][7][8], as a building block for catalysts and auxiliaries [9][10][11], and in materials applications [12][13][14]. New reactions will increase the number of accessible materials that can be made from this biorenewable starting material, particularly if novel approaches for modifying the connectivity of the bicyclic ring system can be developed.…”

Chemically Recyclable Unnatural (1→6)-Polysaccharides from Cellulose-Derived Levoglucosenone and Dihydrolevoglucosenone

“…The successful large-scale production of LGO and Cyrene by Circa Group Ltd. has led to extensive investigations into their applications. LGO is an important optically pure starting material for the chemical synthesis of pharmaceuticals, , and Cyrene is an environmentally friendly solvent. ,− Recently, the use of LGO and Cyrene in the synthesis of polymeric materials has gained attention. − However, in most reported cases, the bicyclic acetal moiety is not used to construct the polymer main chain. Notably, Schlaad and co-workers reported the cROP of LGO-derived levoglucosenyl methyl ether, which could be transformed into (1→6)-polysaccharide derivatives via postpolymerization modification …”