5346-90-7

Basic information

• Product Name: alpha-D-Cellobiose octaacetate
• Synonyms: CELLOBIOSE OCTAACETATE;D-(+)-CELLOBIOSE OCTAACETATE;D-CELLOBIOSE OCTAACETATE;4-O-BETA-D-GLUCOPYRANOSYL-D-GLUCOSE OCTAACETATE;4-O-(2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYL)-1,2,3,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSE;A-D-CELLOBIOSE OCTAACETATE;ALPHA-CELLOBIOSE OCTAACETATE;ALPHA-D-(+)-CELLOBIOSE OCTAACETATE
• CAS NO: 5346-90-7
• Molecular Formula: C₂₈H₃₈O₁₉
• Molecular Weight: 678.59
• EINECS: 226-304-5
• Product Categories: Biochemistry;Disaccharides;O-Substituted Sugars;Sugars;Dextrins、Sugar & Carbohydrates;Base Ingredients;Carbohydrate Sources (Sugars/Extracts);Sugars for Media
• Mol File: 5346-90-7.mol
• Article Data: 1

Chemical Properties

• Melting Point: 225-232 °C
• Boiling Point: 612.2°C (rough estimate)
• Flash Point: 281.178 °C
• Appearance: white powder
• Density: 1.3758 (rough estimate)
• Vapor Pressure: 1.64E-18mmHg at 25°C
• Refractive Index: 40 ° (C=6, CHCl3)
• Storage Temp.: -20°C Freezer
• Solubility: chloroform: 0.1 g/mL, clear, colorless to faintly brownish-
• Stability: Stable at RT
• Merck: 14,1961
• BRN: 79280
• CAS DataBase Reference: alpha-D-Cellobiose octaacetate(CAS DataBase Reference)
• NIST Chemistry Reference: alpha-D-Cellobiose octaacetate(5346-90-7)
• EPA Substance Registry System: alpha-D-Cellobiose octaacetate(5346-90-7)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 24/25-36-26
• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 5346-90-7(Hazardous Substances Data)

Usage

Chemical Properties

white powder

InChI:InChI=1/C28H38O19/c1-11(29)37-9-19-21(39-13(3)31)23(40-14(4)32)26(43-17(7)35)28(46-19)47-22-20(10-38-12(2)30)45-27(44-18(8)36)25(42-16(6)34)24(22)41-15(5)33/h19-28H,9-10H2,1-8H3/t19?,20?,21-,22-,23-,24-,25?,26?,27+,28+/m1/s1

Synthetic route

Cellobiose + acetic anhydride (108-24-7) → α-D-cellobiose octaacetate (5346-90-7)

Conditions	Yield
With perchloric acid at 0 - 20℃;	95%
iron(III) chloride at 28 - 32℃; for 0.5h;	78%
With iodine In dichloromethane at 20℃; for 1h;

Cellobiose (133-99-3, 490-37-9, 2152-98-9, 4482-75-1, 5965-66-2, 13299-27-9, 13360-52-6, 14641-93-1, 15548-43-3, 16462-44-5, 16984-36-4, 16984-38-6, 20869-27-6, 22688-72-8, 27452-49-9, 29276-55-9, 30608-12-9, 34481-13-5, 37169-60-1, 37169-64-5, 64234-01-1, 64234-02-2, 75281-88-8, 80446-85-1, 84413-57-0, 92344-56-4, 93221-87-5, 93301-77-0, 94799-29-8, 100427-98-3, 100428-00-0, 101312-82-7, 102046-24-2, 102046-25-3, 109432-00-0, 109432-02-2, 109432-04-4, 109432-08-8, 135268-49-4, 138231-26-2, 140461-59-2, 145414-22-8, 145414-26-2, 146339-75-5, 146339-76-6, 149116-55-2, 528-50-7) + acetic anhydride (108-24-7) → β-cellobioseoctaacetate (20764-63-0) + α-D-cellobiose octaacetate (5346-90-7)

Conditions	Yield
With pyridine at 20℃; diastereoselective reaction;	A n/a B 95%
With H-Beta zeolite for 48h; Ambient temperature; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
Stage #1: Cellobiose With ammonium chloride; ammonia In methanol at 0℃; for 0.5h; Stage #2: acetic anhydride In pyridine at 20℃; for 12h; Title compound not separated from byproducts;

α-cellobiose (133-99-3, 490-37-9, 2152-98-9, 4482-75-1, 5965-66-2, 13299-27-9, 13360-52-6, 14641-93-1, 15548-43-3, 16462-44-5, 16984-36-4, 16984-38-6, 20869-27-6, 22688-72-8, 27452-49-9, 29276-55-9, 30608-12-9, 34481-13-5, 37169-60-1, 37169-64-5, 64234-01-1, 64234-02-2, 75281-88-8, 80446-85-1, 84413-57-0, 92344-56-4, 93221-87-5, 93301-77-0, 94799-29-8, 100427-98-3, 100428-00-0, 101312-82-7, 102046-24-2, 102046-25-3, 109432-00-0, 109432-02-2, 109432-04-4, 109432-08-8, 135268-49-4, 138231-26-2, 140461-59-2, 145414-22-8, 145414-26-2, 146339-75-5, 146339-76-6, 149116-55-2) + acetic anhydride (108-24-7) → α-D-cellobiose octaacetate (5346-90-7)

Conditions	Yield
With vanadyl triflate at 20℃; for 60h;	85%
With pyridine at 100℃; for 3h; Acetylation;

α-D-glucopyranose-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-2,3,6-triacetate (66073-13-0, 71623-44-4, 101981-29-7, 109922-72-7, 109922-73-8, 132287-75-3, 132287-76-4, 132287-78-6, 132303-63-0, 134311-82-3, 134333-39-4, 18464-08-9) + acetic anhydride (108-24-7) → α-D-cellobiose octaacetate (5346-90-7)

Conditions	Yield
In pyridine Ambient temperature; Yield given;

(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(((2R,3R,4S,5R,6S)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (71692-91-6) + acetic anhydride (108-24-7) → α-D-cellobiose octaacetate (5346-90-7)

Conditions	Yield
With sulfuric acid; hydrogen; palladium on activated charcoal 1.) acetic acid, RT, 40 psi, 2.) 4 h; Yield given. Multistep reaction;

acetic anhydride (108-24-7) + cellulose → α-D-cellobiose octaacetate (5346-90-7)

Conditions	Yield
With sulfuric acid
With sulfuric acid; acetic acid

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) + sodium-compound of/the/ O1,O2,O3,O4-tetraacetyl-β-D-glucopyranose → α-D-cellobiose octaacetate (5346-90-7)

Conditions	Yield
Verschmelzen der 2 Edukte, anschl. mit Acetanhydrid und Natriumacetat;

acetobromocellobiose (14227-66-8) → α-D-cellobiose octaacetate (5346-90-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) mercuric cyanide; 2.) sodium acetate / 1.) 1,2-dichloroethane, 4 d, 40 deg C; 2.) reflux, 20 min 2: pyridine / Ambient temperature View Scheme

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside (19488-48-3) → α-D-cellobiose octaacetate (5346-90-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) 40percent hydrogen bromide, 2.) silver triflate, molecular sieve 4A / 1.) acetic acid, RT, 2 h, 2.) 1,2-dichloroethane, 0 deg C, 1 h 2: 1.) H2, 2.) 4percent sulfuric acid / 1.) 10percent Pd/C / 1.) acetic acid, RT, 40 psi, 2.) 4 h View Scheme

β-D-glucose pentaacetate (604-69-3) → α-D-cellobiose octaacetate (5346-90-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) 40percent hydrogen bromide, 2.) silver triflate, molecular sieve 4A / 1.) acetic acid, RT, 2 h, 2.) 1,2-dichloroethane, 0 deg C, 1 h 2: 1.) H2, 2.) 4percent sulfuric acid / 1.) 10percent Pd/C / 1.) acetic acid, RT, 40 psi, 2.) 4 h View Scheme

Upstream product

• 108-24-7 acetic anhydride 
• 134-96-3 syringic aldehyde 
• 4753-07-5 2,3,6,2',3',4',6'-hepta-O-acetyl-α-D-maltosyl bromide 

Downstream Products

• 7343-99-9 Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-(4-nitro-phenoxy)-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester 
• 125471-64-9 2-O-benzyl-1,3-bis-O-(2,3,6,2',3',4',6'-hepta-O-acetyl-β-lactosyl)glycerol 
• 125471-65-0 3-O-acetyl-2-O-benzyl-1-O-(2,3,6,2',3',4',6'-hepta-O-acetyl-β-lactosyl)-(R,S)-glycerol 
• 160227-12-3 4-methoxyphenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside 
• 67310-53-6 (2R,3S,4S,5R,6S)-2-(acetoxymethyl)-6-(((2R,3R,4S,5R,6R)-4,5-diacetoxy-2-(acetoxymethyl)-6-(benzyloxy)tetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 30854-62-7 lactosyl azide 
• 28022-14-2 phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1->4)-2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranoside 
• 33012-50-9 2,2',3,3',4',6,6'-hepta-O-acetyl-β-D-cellobiosyl azide 
• 14227-66-8 acetobromocellobiose 
• 211676-81-2 Acetic acid (2S,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-(3-mercaptomethyl-benzylsulfanyl)-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester 
• 5346-81-6 phenyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside 
• 495400-10-7 Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-(2-hydroxy-5-nitro-benzyloxy)-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester 
• 495400-11-8 Acetic acid (2R,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-(5-hydroxy-2-nitro-benzyloxy)-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester 
• 726134-69-6 3-(benzyloxycarbonylamino)propyl (2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-β-D-glucopyranoside 

Relevant articles and documents

Synthesis of aryl glycosides as vir gene inducers of Agrobacterium tumefaciens

Aryl β-glycopyranosides have been synthesized by coupling syringaldehyde (3-methoxyvanillin) with L-fucose, D-galactose, and maltose; acetosyringone (4-hydroxy-3,5-dimethoxyacetophenone) with L-fucose and maltose; acetovanillone (4-hydroxy-3-methoxyacetophenone) with L-fucose; and syringic acid (4-hydroxy-3,5-dimethoxybenzoic acid) with D-galactose. The procedure using peracetylated glycosyl halides and sodium phenolates in aqueous acetone afforded the acetylated β-glycosides, which were deacetylated. Aryl β-glycopyranosides have been synthesized by coupling syringaldehyde (3-methoxyvanillin) with L-fucose, D-galactose, and maltose; acetosyringone (4-hydroxy-3,5-dimethoxyacetophenone) with L-fucose and maltose; acetovanillone (4-hydroxy-3-methoxyacetophenone) with L-fucose; and syringic acid (4-hydroxy-3,5-dimethoxybenzoic acid) with D-galactose. The procedure using peracetylated glycosyl halides and sodium phenolates in aqueous acetone afforded the acetylated β-glycosides, which were deacetylated.