35405-71-1

Basic information

• Product Name: 1,6-Anhydro-b-D-cellobiose
• Synonyms: 1,6-Anhydro-b-D-cellobiose;Cellobiosan;1,6-Anhydro-4-O-β-D-glucopyranosyl-β-D-glucopyranose;1,6-Anhydro-β-cellobiose;1,6-Anhydro-beta-D-cellobiose min. 98%;1,6-ANHYDRO-BETA-D-CELLOBIOSE
• CAS NO: 35405-71-1
• Molecular Formula: C₁₂H₂₀O₁₀
• Molecular Weight: 324.28
• Product Categories: Oligosaccharides
• Mol File: 35405-71-1.mol
• Article Data: 5

Chemical Properties

• Melting Point: 183 °C(Solv: ethanol (64-17-5))
• Boiling Point: 640.323oC at 760 mmHg
• Flash Point: 341.055oC
• Appearance: White to Off-white/Powder
• Density: 1.741g/cm3
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.644
• PKA: 12.88±0.70(Predicted)
• Water Solubility: Soluble in water at 50mg/ml
• CAS DataBase Reference: 1,6-Anhydro-b-D-cellobiose(CAS DataBase Reference)
• NIST Chemistry Reference: 1,6-Anhydro-b-D-cellobiose(35405-71-1)
• EPA Substance Registry System: 1,6-Anhydro-b-D-cellobiose(35405-71-1)

Safety Data

• Hazardous Substances Data: 35405-71-1(Hazardous Substances Data)

Usage

Description

Cellobiosan is an anhydro sugar formed during biofuel production from the fast pyrolysis of wood.

Uses

A common anhydro sugar in wood pyrolysis oils.

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 
• 13360-52-6 Cellobiose 
• 69429-19-2 1,4-β-cellotriose 
• 20702-56-1 O-β-D-glucopyranosyl-(1->4)-O-β-D-glucopyranosyl-(1->4)-O-β-D-glucopyranosyl-(1->4)-β-D-glucopyranose 
• 78797-67-8 O-β-D-glucopyranosyl-(1->4)-O-β-D-glucopyranosyl-(1->4)-1,6-anhydro-β-D-glucopyranose 
• 122274-98-0 1,6-anhydro cellopentaose 
• 138902-21-3 1,6-Anhydro-2,3-di-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-β-D-glucopyranose 
• 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 
• 104976-44-5 1,6-Anhydro-2,3-di-O-benzyl-4-O-<(trifluormethyl)sulfonyl>-β-D-galactopyranose 
• 95335-96-9 2,3,4-Tri-O-benzyl-6-O-(monomethoxytrityl)-D-mannose 
• 61074-29-1 1,6-Anhydro-2,3-di-O-benzyl-β-D-galactopyranose 
• 170998-51-3 1,6-Anhydro-2,3-di-O-benzyl-4-O-nonafluorobutanesulfonyl-β-D-galactopyranose 
• 4132-28-9 2,3,4,6-tetra-O-benzyl-D-mannopyranose 
• 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 

Downstream Products

• 56838-36-9 1,6-anhydro-4-O-(4,6-O-benzylidene-β-D-glucopyranosyl)-β-D-glucopyranose 
• 7081-62-1 1,6-anhydro-6'-O-trityl-β-cellobiose 
• 492-61-5 β-D-glucose 
• 498-07-7 levoglucosan 
• 97390-18-6 1,6-anhydro-4-O-(4,6-O-benzylidene-β-D-glucopyranosyl)-2,3-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-glucopyranose 
• 97390-32-4 O-(3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-1,6-anhydro-2,3-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-glucopyranose 
• 97390-26-6 O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-1,6-anhydro-2,3-O-(tetraisopropyldisiloxane-1,3-diyl)-β-D-glucopyranose 
• 97390-30-2 2,3-di-O-acetyl-1,6-anhydro-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-β-D-glucopyranose 
• 97390-20-0 1,6-anhydro-4-O-<4,6-O-benzylidene-2,3-di-O-(N-phenylcarbamoyl)-β-D-glucopyranosyl>-2,3-O-(tetraisopropyldisiloxane-1,3-diyl)-β-glucopyranose 
• 97390-31-3 (2R,4aR,6S,7R,8S,8aS)-7-Benzyloxy-2-phenyl-6-((1R,2R,8S,9R,10R)-4,4,6,6-tetraisopropyl-3,5,7,12,13-pentaoxa-4,6-disila-tricyclo[8.2.1.0^2,8]tridec-9-yloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol 
• 97390-16-4 1,6-anhydro-2,3-O-(tetraisopropyldisiloxane-1,3-diyl)-4-O-(2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranyl)-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 
• 97390-28-8 1,6-anhydro-4-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-β-D-glucopyranose 
• 135362-94-6 C₂₆H₃₀O₁₂S 

Relevant articles and documents

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.

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.

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