35405-71-1

Usage

Uses

Used in Biofuel Production:
1,6-Anhydro-b-D-cellobiose is used as an intermediate in the production of biofuels from wood, as it is formed during the fast pyrolysis process. Its presence in wood pyrolysis oils indicates its potential role in the conversion of lignocellulosic biomass into valuable bioproducts.
Used in Chemical Industry:
1,6-Anhydro-b-D-cellobiose can be used as a building block for the synthesis of various chemicals and materials, such as polymers, pharmaceuticals, and other bioactive compounds. Its unique structure and properties make it a valuable starting material for the development of novel products in the chemical industry.
Used in Pharmaceutical Research:
Due to its structural similarity to cellulose, 1,6-Anhydro-b-D-cellobiose may be used in the development of new drugs and therapies targeting cellulose-related diseases or conditions. It can also serve as a model compound for studying the interactions between cellulose and enzymes or other biomolecules, which could lead to the discovery of new pharmaceutical agents.
Used in Material Science:
1,6-Anhydro-b-D-cellobiose can be utilized in the development of new materials with unique properties, such as biodegradable plastics, adhesives, and coatings. Its ability to form complexes with other molecules makes it a promising candidate for the creation of advanced materials with specific functionalities.

InChI:InChI=1/C12H20O10/c13-1-3-5(14)6(15)8(17)12(20-3)22-10-4-2-19-11(21-4)9(18)7(10)16/h3-18H,1-2H2/t3?,4?,5-,6+,7-,8?,9?,10-,11-,12+/m1/s1

Upstream product

• 9004-34-6 cellulose 
• 104976-44-5 1,6-Anhydro-2,3-di-O-benzyl-4-O-<(trifluormethyl)sulfonyl>-β-D-galactopyranose 
• 4132-28-9 2,3,4,6-tetra-O-benzyl-D-mannopyranose 
• 113842-46-9 O-(4-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->4)-1,6-anhydro-2,3-di-O-benzyl-β-D-glucopyranose 
• 86461-99-6 (2R,3R,4S,5R,6R)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-((1R,2R,3R,4R,5R)-3,4-bis-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-tetrahydro-pyran-3-ol 
• 170998-51-3 1,6-Anhydro-2,3-di-O-benzyl-4-O-nonafluorobutanesulfonyl-β-D-galactopyranose 
• 61074-29-1 1,6-Anhydro-2,3-di-O-benzyl-β-D-galactopyranose 
• 95335-96-9 2,3,4-Tri-O-benzyl-6-O-(monomethoxytrityl)-D-mannose 
• 170998-52-4 1,6-Anhydro-2,3-di-O-benzyl-4-O-<2,3,4-tri-O-benzyl-6-O-(p-methoxyphenyl)diphenylmethyl-α-D-mannopyranosyl>-β-D-glucopyranose 
• 122274-98-0 1,6-anhydro cellopentaose 
• 78797-67-8 O-β-D-glucopyranosyl-(1->4)-O-β-D-glucopyranosyl-(1->4)-1,6-anhydro-β-D-glucopyranose 
• 20702-56-1 O-β-D-glucopyranosyl-(1->4)-O-β-D-glucopyranosyl-(1->4)-O-β-D-glucopyranosyl-(1->4)-β-D-glucopyranose 
• 69429-19-2 1,4-β-cellotriose 
• 13360-52-6 Cellobiose 

Downstream Products

• 38631-27-5 2,3-Di-O-acetyl-1,6-anhydro-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranose 
• 492-61-5 β-D-glucose 
• 498-07-7 levoglucosan 
• 92840-78-3 1,6-anhydro-4-O-(4,6-O-isopropylidene-β-D-glucopyranosyl)-2-O-p-tolylsulfonyl-β-D-glucopyranose 
• 97465-52-6 1,6-anhydro-2,3-di-O-benzyl-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-β-D-glucopyranose 
• 99541-22-7 O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-1,6:2,3-dianhydro-β-D-mannopyranose 
• 150126-09-3 C₁₉H₂₂O₉ 
• 135362-94-6 C₂₆H₃₀O₁₂S 
• 86032-62-4 1,6-anhydro-2,3-di-O-benzoyl-4-O-(2,3,4-tri-O-benzoyl-6-O-trityl-β-D-glucopyranosyl)-β-D-glucopyranose 
• 86032-75-9 1,6-anhydro-2,3-di-O-benzoyl-4-O-(2,3,4-tri-O-benzoyl-6-O-trityl-α-L-idopyranosyl)-β-D-glucopyranose 
• 86032-65-7 1,6-anhydro-2,3-di-O-benzyl-4-O-(2,3,4-tri-O-benzyl-6-O-trityl-β-D-glucopyranosyl)-β-D-glucopyranose 
• 86032-63-5 1,6-anhydro-2,3-di-O-benzoyl-4-O-(methyl 2,3,4-tri-O-benzoyl-β-D-glucopyranosyluronate)-β-D-glucopyranose 
• 86032-76-0 1,6-anhydro-2,3-di-O-benzoyl-4-O-(methyl 2,3,4-tri-O-benzoyl-α-L-idopyranosyluronate)-β-D-glucopyranose 

Relevant academic research and scientific papers

Mass spectrometric studies of fast pyrolysis of cellulose

A fast pyrolysis probe/linear quadrupole ion trap mass spectrometer combination was used to study the primary fast pyrolysis products (those that first leave the hot pyrolysis surface) of cellulose, cellobiose, cellotriose, cellotetraose, cellopentaose, and cellohexaose, as well as of cellobiosan, cellotriosan, and cellopentosan, at 600°C. Similar products with different branching ratios were found for the oligosaccharides and cellulose, as reported previously. However, identical products (with the exception of two) with similar branching ratios were measured for cellotriosan (and cellopentosan) and cellulose. This result demonstrates that cellotriosan is an excellent small-molecule surrogate for studies of the fast pyrolysis of cellulose and also that most fast pyrolysis products of cellulose do not originate from the reducing end. Based on several observations, the fast pyrolysis of cellulose is suggested to initiate predominantly via two competing processes: The formation of anhydro-oligosaccharides, such as cellobiosan, cellotriosan, and cellopentosan (major route), and the elimination of glycolaldehyde (or isomeric) units from the reducing end of oligosaccharides formed from cellulose during fast pyrolysis.

High-pressure fast-pyrolysis, fast-hydropyrolysis and catalytic hydrodeoxygenation of cellulose: Production of liquid fuel from biomass

A lab-scale, high-pressure, continuous-flow fast-hydropyrolysis and vapor-phase catalytic hydrodeoxygenation (HDO) reactor has been successfully designed, built and tested with cellulose as a model biomass feedstock. We investigated the effects of pyrolysis temperature on high-pressure cellulose fast-pyrolysis, hydrogen on high-pressure cellulose fast-hydropyrolysis, reaction pressure (27 bar and 54 bar) on our reactor performance and candidate catalysts for downstream catalytic HDO of cellulose fast-hydropyrolysis vapors. In this work, a liquid chromatography-mass spectrometry (LC-MS) method has been developed and utilized for quantitative characterization of the liquid products. The major compounds in the liquid from cellulose fast-pyrolysis (27 bar, 520 °C) are levoglucosan and its isomers, formic acid, glycolaldehyde, and water, constituting 51 wt%, 11 wt%, 8 wt% and 24 wt% of liquid respectively. Our results show that high pressures of hydrogen do not have a significant effect on the fast-hydropyrolysis of cellulose at 480 °C but suppress the formation of reactive light oxygenate species like glycolaldehyde and formic acid at 580 °C. The formation of permanent gases (CO, CO2, CH4) and glycolaldehyde and formic acid increased with increasing pyrolysis temperature in the range of 480 °C-580 °C in high-pressure cellulose fast-pyrolysis, in the absence of hydrogen. Candidate HDO catalysts Al 2O3, 2% Ru/Al2O3 and 2% Pt/Al 2O3 resulted in extents of deoxygenation of 20%, 22% and 27%, respectively, but led to carbon loss to gas phase as CO and CH4. These catalysts provide useful insights for other candidate HDO catalysts for improving the extent of deoxygenation with higher carbon recovery in the liquid product.

EFFECT OF PROTECTING GROUPS AND SOLVENTS IN ANOMERIC O-ALKYLATION OF MANNOPYRANOSE

Anomeric O-alkylation of mannopyranoses with various protecting groups was investigated using mannose derivatives and 2,3-O-isopropylidene-1-O-trifluoromethanesulfonyl-D-glycerol (1) as alkylating agent.Generally, in polar solvents higher α/β ratios were obtained than in nonpolar solvents.Sterically demanding protecting groups at the 6-O-position and polar solvents led to higher yields.Reactivity differences were explained by different complex formation.Based on these results mannopyranosyl-α(1-4)glucopyranosides 26 and 27 were synthesized using mannose derivatives 5 and 6 having a 6-O-(p-methoxyphenyl)diphenylmethyl group and galactosyl trifluoromethanesulfonate 24 or nonafluorobutanesulfonate (nonaflate) 25, respectively, as alkylating agents.

Anomeric O-Alkylation, 9. Disaccharide Synthesis via Anomeric O-Alkylation

Base-promoted reaction of tetra-O-benzyl-glucose 1a with secondary alkyl trifluoromethanesulfonates 2 and 3 in toluene provides in the presence of 15-crown-5 preferentially β-glycosides 2aβ and 3aβ, respectively, in high yields.For reactions carried out a

TOTAL SYNTHESIS OF CYCLOMALTOHEXAOSE

Described for the first time is a total synthesis of cyclomaltohexaose, in 0.3percent overall yield, in 21 steps starting from maltose.Maltose was transformed into allyl O-(2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranosi