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CAS No.: | 5346-90-7 |
---|---|
Name: | alpha-D-Cellobiose octaacetate |
Molecular Structure: | |
Formula: | C28H38O19 |
Molecular Weight: | 678.598 |
Synonyms: | Cellobiose,octaacetate, a-D-(8CI);a-D-Glucopyranose, 4-O-(2,3,4,6-tetra-O-acetyl-b-D-glucopyranosyl)-, tetraacetate(9CI);NSC 1221;NSC 1696;Octa-O-acetyl-a-D-cellobiose;Octaacetyl-a-cellobiose;a-Cellobiopyranose octaacetate;a-Cellobiose octaacetate;a-D-Cellobiose octaacetate; |
EINECS: | 226-304-5 |
Density: | 1.37 g/cm3 |
Melting Point: | 225-232 °C |
Boiling Point: | 683.055 °C at 760 mmHg |
Flash Point: | 281.178 °C |
Solubility: | chloroform: 0.1 g/mL, clear, colorless to faintly brownish-yellow |
Appearance: | white powder |
Hazard Symbols: | Xn |
Risk Codes: | 20/21/22-36/37/38 |
Safety: | 24/25-36-26 |
PSA: | 238.09000 |
LogP: | -0.83080 |
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
acetic anhydride
A
β-cellobioseoctaacetate
B
α-D-cellobiose octaacetate
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
acetic anhydride
α-D-cellobiose octaacetate
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
acetic anhydride
α-D-cellobiose octaacetate
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
acetic anhydride
α-D-cellobiose octaacetate
Conditions | Yield |
---|---|
With sulfuric acid; hydrogen; palladium on activated charcoal 1.) acetic acid, RT, 40 psi, 2.) 4 h; Yield given. Multistep reaction; |
Conditions | Yield |
---|---|
With sulfuric acid | |
With sulfuric acid; acetic acid |
Conditions | Yield |
---|---|
Verschmelzen der 2 Edukte, anschl. mit Acetanhydrid und Natriumacetat; |
acetobromocellobiose
α-D-cellobiose octaacetate
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
α-D-cellobiose octaacetate
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 |
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 |
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