3891-59-6

Basic information

• Product Name: alpha-D-Glucose pentaacetate
• Synonyms: 2,3,4,5,6-Penta-O-acetylhexose;alpha-d-Glucose 2,3,4,5,6-pentaacetate;d-Allose, pentaacetate(ester);Glucose acetate;Gulose pentaacetate;Pentaacetylglucose;D-GLUCOSE PENTAACETATE;1,2,3,4,6-PENTA-O-ACETYL-D-GLUCOPYRANOSE
• CAS NO: 3891-59-6
• Molecular Formula: C₁₆H₂₂O₁₁
• Molecular Weight: 390.34
• EINECS: 223-439-1
• Mol File: 3891-59-6.mol
• Article Data: 23

Chemical Properties

• Melting Point: 110°C
• Boiling Point: 435.58°C (rough estimate)
• Flash Point: 188.1 °C
• Appearance: White crystalline powder
• Density: 1.3984 (rough estimate)
• Refractive Index: 1.5376 (estimate)
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Water Solubility: < 5 G/L (25℃)
• CAS DataBase Reference: alpha-D-Glucose pentaacetate(CAS DataBase Reference)
• NIST Chemistry Reference: alpha-D-Glucose pentaacetate(3891-59-6)
• EPA Substance Registry System: alpha-D-Glucose pentaacetate(3891-59-6)

Safety Data

• Safety Statements: S24/25:
• Hazardous Substances Data: 3891-59-6(Hazardous Substances Data)

Usage

Chemical Properties

Different sources of media describe the Chemical Properties of 3891-59-6 differently. You can refer to the following data:
1. White solid
2. Glucose pentaacetate is odorless, but has a bitter favor.

Preparation

By acetylation of glucose using any number of techniques, including ZnCl2 and pyridine, sodium acetate, and acetic anhydride and pyridine.

Taste threshold values

Taste characteristics at 100 ppm: bitter-like with a citrus tonic favor.

InChI:InChI=1/C16H22O11/c1-7(17)22-6-12-13(23-8(2)18)14(24-9(3)19)15(25-10(4)20)16(27-12)26-11(5)21/h12-16H,6H2,1-5H3/t12?,13-,14+,15+,16+/m1/s1

Synthetic route

D-glucose (50-99-7) + acetic anhydride (108-24-7) → Penta-O-acetyl-aldehydo-D-glucose (3891-59-6)

Conditions	Yield
In 1-butyl-3-methylimidazolium methyl phosphonate at 20℃; for 15h;	92%
With pyridine; N-Bromosuccinimide; hydrogen cation; ethanethiol Multistep reaction;
With pyridine at 20℃; for 24h;
With pyridine at 20℃; for 22h;	2.1 mg
With perchloric acid In chloroform at 10℃; for 3h;

2,3,4,5,6-penta-O-acetyl-D-glucose diethyl dithioacetal (4984-72-9) → Penta-O-acetyl-aldehydo-D-glucose (3891-59-6)

Conditions	Yield
With water; mercury dichloride; mercury(II) oxide In acetone for 48h; Product distribution; Ambient temperature; reagent, time, temperature;	79%
Stage #1: 2,3,4,5,6-penta-O-acetyl-D-glucose diethyl dithioacetal With 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride In dichloromethane at -60℃; for 0.333333h; Stage #2: With water In tetrahydrofuran; dichloromethane at -60 - 20℃;	78%
With N-Bromosuccinimide; cadmium(II) carbonate; water In acetone at 0℃; for 0.05h;	77%

penta-O-acetyl-aldehydo-D-glucose oxime → Penta-O-acetyl-aldehydo-D-glucose (3891-59-6)

Conditions	Yield
With hydrogenchloride; ethanol; sodium nitrite

penta-O-acetyl-aldehydo-D-glucose-(acetyl-formyl-hydrazone) → Penta-O-acetyl-aldehydo-D-glucose (3891-59-6)

Conditions	Yield
With selenium(IV) oxide; acetic anhydride; acetic acid

acetic anhydride (108-24-7) + (Z)-6α-(β-D-glucosyloxy)-4α,5α-dihydroxy-2-cyclohexene-Δ1,α-acetonitrile (84799-31-5) → Penta-O-acetyl-aldehydo-D-glucose (3891-59-6) + Acetic acid (1S,5R,6R)-5,6-diacetoxy-2-[1-cyano-meth-(Z)-ylidene]-cyclohex-3-enyl ester

Conditions	Yield
With pyridine; β-glucosidase Multistep reaction;

2-acetamido-2-deoxy-3,4,5,6-tetra-O-acetyl-D-mannose (122383-00-0) → Penta-O-acetyl-aldehydo-D-glucose (3891-59-6)

Conditions	Yield
With dimethylsulfide; ozone 1.) CH2Cl2, -78 deg C, 11 h, 2.) -78 deg C to RT, 4 h; Yield given. Multistep reaction;

2,3,4,5,6-penta-O-acetyl-D-glucose diethyl dithioacetal (4984-72-9) + bromine (7726-95-6) + acetic acid (64-19-7) → Penta-O-acetyl-aldehydo-D-glucose (3891-59-6)

selenium(IV) oxide (7446-08-4) + penta-O-acetyl-aldehydo-D-glucose-(acetyl-formyl-hydrazone) + acetic anhydride (108-24-7) + acetic acid (64-19-7) → Penta-O-acetyl-aldehydo-D-glucose (3891-59-6)

penta-O-acetyl-aldehydo-D-gluconoyl chloride → Penta-O-acetyl-aldehydo-D-glucose (3891-59-6)

Conditions	Yield
With Pd-BaSO4; xylene Hydrogenation;

penta-O-acetyl-aldehydo-D-glucose-ethanediylsulfanylacetal → Penta-O-acetyl-aldehydo-D-glucose (3891-59-6)

Conditions	Yield
With bromine; acetic acid

hydrogenchloride (7647-01-0) + ethanol (64-17-5) + penta-O-acetyl-aldehydo-D-glucose oxime + sodium nitrite → Penta-O-acetyl-aldehydo-D-glucose (3891-59-6)

N-acetyl-D-mannosamine (14131-64-7) → Penta-O-acetyl-aldehydo-D-glucose (3891-59-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: pyridine / 4 h / Ambient temperature 2: dimethylaminopyridine / pyridine / 12 h 3: 1.) O3, 2.) dimethyl sulfide / 1.) CH2Cl2, -78 deg C, 11 h, 2.) -78 deg C to RT, 4 h View Scheme

N-[(1R,2R,3S,4R)-2,3,4,5-Tetrahydroxy-1-(methoxyimino-methyl)-pentyl]-acetamide (54220-78-9, 54220-79-0, 54220-80-3) → Penta-O-acetyl-aldehydo-D-glucose (3891-59-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: dimethylaminopyridine / pyridine / 12 h 2: 1.) O3, 2.) dimethyl sulfide / 1.) CH2Cl2, -78 deg C, 11 h, 2.) -78 deg C to RT, 4 h View Scheme

indioside I (174761-03-6) + acetic anhydride (108-24-7) → Penta-O-acetyl-aldehydo-D-glucose (3891-59-6)

Conditions	Yield
Stage #1: indioside I With hydrogenchloride In 1,4-dioxane at 90℃; Stage #2: acetic anhydride With pyridine In 1,4-dioxane at 60℃;

indioside J (1365309-19-8) + acetic anhydride (108-24-7) → Penta-O-acetyl-aldehydo-D-glucose (3891-59-6)

Conditions	Yield
Stage #1: indioside J With hydrogenchloride In 1,4-dioxane at 90℃; Stage #2: acetic anhydride With pyridine In 1,4-dioxane at 60℃;

acidic polysaccharide AMP40S + acetic anhydride (108-24-7) → D-erythritol tetraacetate (866394-64-1) + Penta-O-acetyl-aldehydo-D-glucose (3891-59-6) + triacetylglycerol (102-76-1) + 2,3,4,5-tetra-O-acetyl-aldehydo-L-rhamnose

Conditions	Yield
Stage #1: acidic polysaccharide AMP40S With sodium periodate; sodium iodate In water at 4℃; Darkness; Stage #2: With sodium tetrahydroborate In water at 25℃; for 20h; Stage #3: acetic anhydride Further stages;

Penta-O-acetyl-aldehydo-D-glucose (3891-59-6) + 2-methylpropan-2-thiol (75-66-1) → Acetic acid (1S,2R,3R)-2,3,4-triacetoxy-1-((R)-1-acetoxy-2,2-bis-tert-butylsulfanyl-ethyl)-butyl ester (112288-76-3)

Conditions	Yield
With boron trifluoride diethyl etherate In chloroform for 0.666667h; Ambient temperature;	91%

Penta-O-acetyl-aldehydo-D-glucose (3891-59-6) + 1-aminoguanidine hydrochloride (1937-19-5) → C17H26N4O10*ClH (109853-93-2)

Conditions	Yield
In water for 5h;	86%

Penta-O-acetyl-aldehydo-D-glucose (3891-59-6) → 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8)

Conditions	Yield
With hydrogen bromide In dichloromethane; acetic acid at 20℃; for 6h;	86%
With hydrogen bromide In acetic acid

L-Cysteine (52-90-4) + Penta-O-acetyl-aldehydo-D-glucose (3891-59-6) → 2(RS)-D-gluco-(1',2',3',4',5'-pentacetoxypentyl)thiazolidine-4(R)-carboxylic acid (57993-69-8, 97334-95-7, 110270-26-3, 110270-27-4, 110270-28-5)

Conditions	Yield
In water	85.9%

Penta-O-acetyl-aldehydo-D-glucose (3891-59-6) + CH6N4*H2O*HNO3 → C17H26N4O10*HNO3 (109853-95-4)

Conditions	Yield
In water for 5h;	82%

Penta-O-acetyl-aldehydo-D-glucose (3891-59-6) + 4-(4-methoxy-phenyl)-3-methyl-benzo[f]quinolinium; perchlorate → 4-(4-Methoxy-phenyl)-3-((E)-(3S,4R,5R,6R)-3,4,5,6,7-pentaacetoxy-hept-1-enyl)-benzo[f]quinolinium; perchlorate

Conditions	Yield
With pyridine at 60 - 70℃; for 1h;	81%

Penta-O-acetyl-aldehydo-D-glucose (3891-59-6) + 1-p-Methoxyphenyl-6-methoxyquinaldine perchlorate → 6-Methoxy-1-(4-methoxy-phenyl)-2-((E)-(3S,4R,5R,6R)-3,4,5,6,7-pentaacetoxy-hept-1-enyl)-quinolinium; perchlorate

Conditions	Yield
With pyridine at 60 - 70℃; for 1h;	73%

Penta-O-acetyl-aldehydo-D-glucose (3891-59-6) + 3-methyl-4-p-tolyl-benzo[f]quinolinium; iodide (52529-67-6) → 3-((E)-(3S,4R,5R,6R)-3,4,5,6,7-Pentaacetoxy-hept-1-enyl)-4-p-tolyl-benzo[f]quinolinium; iodide (75759-76-1, 75801-17-1)

Conditions	Yield
With pyridine at 60 - 70℃; for 1h;	72%

p-hydroxycinnamoylfilicinic acid (867296-31-9) + Penta-O-acetyl-aldehydo-D-glucose (3891-59-6) → C40H42O15

Conditions	Yield
Stage #1: p-hydroxycinnamoylfilicinic acid; Penta-O-acetyl-aldehydo-D-glucose With sodium methylate In methanol at 20℃; for 8h; Stage #2: With sodium methylate In methanol at 20℃; for 1h;	71%

Penta-O-acetyl-aldehydo-D-glucose (3891-59-6) + 6-Bromo-1-(4-bromo-phenyl)-2-methyl-quinolinium; perchlorate → 6-Bromo-1-(4-bromo-phenyl)-2-((E)-(3S,4R,5R,6R)-3,4,5,6,7-pentaacetoxy-hept-1-enyl)-quinolinium; perchlorate

Conditions	Yield
With pyridine	67%

Penta-O-acetyl-aldehydo-D-glucose (3891-59-6) + O-allylhydroxylamine trifluoroacetic acid salt + acetic anhydride (108-24-7) → (2R,3R,4R,5S)-6-(allyloxyimino)hexane-1,2,3,4,5-pentayl pentaacetate

Conditions	Yield
Stage #1: Penta-O-acetyl-aldehydo-D-glucose; O-allylhydroxylamine trifluoroacetic acid salt With pyridine at 60℃; for 2.5h; Inert atmosphere; Stage #2: acetic anhydride With pyridine; N,N-dimethyl-formamide for 16h; Inert atmosphere;	66%

Penta-O-acetyl-aldehydo-D-glucose (3891-59-6) + 3-methyl-4-phenylbenzoquinolinium iodide (52529-64-3) → 3-((E)-(3S,4R,5R,6R)-3,4,5,6,7-Pentaacetoxy-hept-1-enyl)-4-phenyl-benzo[f]quinolinium; iodide (75759-74-9, 75801-90-0)

Conditions	Yield
With pyridine at 60 - 70℃; for 1h;	65%

Penta-O-acetyl-aldehydo-D-glucose (3891-59-6) + 1,3-Dimethoxybenzene (151-10-0) → 2,3,4,5,6-penta-O-acetyl-1-deoxy-1,1-bis(2,4-dimethoxyphenyl)-D-glucitol + Acetic acid (1S,2R,3R,4R)-2,3,4,5-tetraacetoxy-1-[(S)-{2,4-dimethoxy-5-[(1R,2S,3R,4R,5R)-2,3,4,5,6-pentaacetoxy-1-(2,4-dimethoxy-phenyl)-hexyl]-phenyl}-(2,4-dimethoxy-phenyl)-methyl]-pentyl ester

Conditions	Yield
With boron trifluoride diethyl etherate In dichloromethane at 20℃; for 1.5h;	A 56% B n/a

Penta-O-acetyl-aldehydo-D-glucose (3891-59-6) + acetic anhydride (108-24-7) → 1,1,2,3,4,5,6-hepta-O-acetylaldehydo-D-glucose aldehydrol (10356-82-8, 118380-74-8, 17296-20-7)

Conditions	Yield
With pyridine at 20℃; for 2h;	45%

Penta-O-acetyl-aldehydo-D-glucose (3891-59-6) + 2,6-dimethyl-1-p-tolyl-quinolinium; perchlorate → 6-Methyl-2-((E)-(3S,4R,5R,6R)-3,4,5,6,7-pentaacetoxy-hept-1-enyl)-1-p-tolyl-quinolinium; perchlorate

Conditions	Yield
With pyridine	43%

Penta-O-acetyl-aldehydo-D-glucose (3891-59-6) + mercaptoacetic acid (68-11-1) → Acetic acid (1S,2R,3R)-2,3,4-triacetoxy-1-[(R)-acetoxy-(5-oxo-[1,3]oxathiolan-2-yl)-methyl]-butyl ester (114413-08-0, 114413-11-5, 114488-72-1, 114488-73-2)

Conditions	Yield
In benzene Heating;	43%

Penta-O-acetyl-aldehydo-D-glucose (3891-59-6) + cyanoacetic acid amide (107-91-5) → (2E,4E)(6R,7R)-4,6,7,8-tetraacetoxy-2-cyano-octadienamide (120331-74-0)

Conditions	Yield
With 4 A molecular sieve In pyridine Ambient temperature;	42.1%

Penta-O-acetyl-aldehydo-D-glucose (3891-59-6) + 2-methyl-1-ethylquinolinium perchlorate → 1-Ethyl-2-((E)-(3S,4R,5R,6R)-3,4,5,6,7-pentaacetoxy-hept-1-enyl)-quinolinium; perchlorate

Conditions	Yield
With pyridine	42%

Penta-O-acetyl-aldehydo-D-glucose (3891-59-6) + N-phenylquinaldinium perchlorate → α-(1-phenylquinolin-2)-β--dimethine perchlorate

Conditions	Yield
With pyridine for 1h;	40%

p-hydroxycinnamoylfilicinic acid (867296-31-9) + Penta-O-acetyl-aldehydo-D-glucose (3891-59-6) → Acetic acid (1S,2R,3R,4R)-2,3,4,5-tetraacetoxy-1-(bis-{2,4-dihydroxy-5-[(E)-3-(4-hydroxy-phenyl)-acryloyl]-3,3-dimethyl-6-oxo-cyclohexa-1,4-dienyl}-methyl)-pentyl ester

Conditions	Yield
With sodium methylate In methanol at 20℃; for 8h;	39%

Penta-O-acetyl-aldehydo-D-glucose (3891-59-6) + 1,2-dimethylquinolinium perchlorate → 1-Methyl-2-((E)-(3S,4R,5R,6R)-3,4,5,6,7-pentaacetoxy-hept-1-enyl)-quinolinium; perchlorate

Conditions	Yield
With pyridine	38%

Penta-O-acetyl-aldehydo-D-glucose (3891-59-6) + 2-methyl-1-[1]naphthyl-quinolinium; perchlorate → 1-Naphthalen-1-yl-2-((E)-(3S,4R,5R,6R)-3,4,5,6,7-pentaacetoxy-hept-1-enyl)-quinolinium; perchlorate

Conditions	Yield
With pyridine	37%

Penta-O-acetyl-aldehydo-D-glucose (3891-59-6) + acetylacetone (123-54-6) → trans-4-(D-gluco-penta-acetoxypentyl)-3-buten-2-one (10399-90-3)

Conditions	Yield
piperidine In ethanol for 48h; Ambient temperature;	33.2%

Penta-O-acetyl-aldehydo-D-glucose (3891-59-6) + acetylacetone (123-54-6) → Acetic acid (1R,2S)-2-acetoxy-4-acetyl-5-oxo-1-((1R,2R)-1,2,3-triacetoxy-propyl)-hex-3-enyl ester (83162-45-2)

Conditions	Yield
With pyridine; titanium tetrachloride In tetrahydrofuran; tetrachloromethane at 0℃; for 48h;	15%

Penta-O-acetyl-aldehydo-D-glucose (3891-59-6) + dichloroacetic acid methyl ester (116-54-1) → methyl 2,3-anhydro-2-chloro-4,5,6,7,8-penta-O-acetyl-D-glucooctonoate (125967-07-9)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide; benzene at 5℃;	12%

diazomethane (186581-53-3, 908094-01-9) + Penta-O-acetyl-aldehydo-D-glucose (3891-59-6) → 1-Deoxy-3,4,5,6,7-penta-O-acetyl-L-gulo-2-heptulose (83615-60-5)

Conditions	Yield
With methanol; diethyl ether; chloroform

diazomethane (186581-53-3, 908094-01-9) + Penta-O-acetyl-aldehydo-D-glucose (3891-59-6) → penta-O-acetyl-keto-D-gluco-1,2-dideoxy-[3]octulose (109568-68-5)

Conditions	Yield
With diethyl ether; chloroform

4,6-diamino-2-methylthiopyrimidine (1005-39-6) + Penta-O-acetyl-aldehydo-D-glucose (3891-59-6) + 2,5-dichlorobenzenediazonium (15470-55-0) → O2,O3,O4,O6-tetraacetyl-D-glucose-[6-amino-5-(2,5-dichloro-phenylazo)-2-methylsulfanyl-pyrimidin-4-ylimine]

Conditions	Yield
ueber mehrere Stufen;

Upstream product

• 50-99-7 D-glucose 
• 108-24-7 acetic anhydride 
• 81969-64-4 1,6-Anhydro-α-L-idohexofuranose 
• 72003-68-0 2,3,4,5,6-penta-O-acetyl-D-galactose diethyl dithioacetal 
• 1372610-16-6 1,2,3,4,5-penta-O-acetyl-D-galactitol 
• 1372792-90-9 1,2,3,4,5-penta-O-acetyl-6-O-benzyl-D-galactitol 
• 129941-51-1 1,2,3,4,5-penta-O-acetyl-6-S-phenyl-6-thio-D-galactitol 
• 129905-50-6 2,3,4,5,6-penta-O-acetyl-1-chloro-S-phenyl-1-thio-L-galactitol 
• 128333-82-4 3,4,5,6,7-penta-O-acetyl-1,2-dideoxy-L-galacto-hept-1-enitol 
• 1365309-19-8 indioside J 
• 174761-03-6 indioside I 
• 7647-01-0 hydrogenchloride 
• 64-17-5 ethanol 
• 7446-08-4 selenium(IV) oxide 

Downstream Products

• 4064-06-6 1,2:3,4-di-O-isopropylidene-α-L-galactopyranose 
• 15572-79-9 aldehydo-L-Galactose 
• 112137-62-9 (1Ξ)-O²,O³,O⁴,O⁵,O⁶-pentaacetyl-1-dimethoxyphosphoryl-D-glucitol 
• 18604-50-7 eugenyl glucoside 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 106991-16-6 1-Hydroxy-1-methyl-3--2,4-bis-aethoxycarbonyl-cyclohexan-5-on 
• 849585-22-4 LACTIC ACID 
• 89243-20-9 1',1'-bis<3-methyl-5-oxo-1-phenyl-Δ²-4-pyrazyl>-1'-deoxy-2',3',4',5',6'-penta-O-acetyl-D-glucitol 
• 75759-76-1 3-((E)-(3S,4R,5R,6R)-3,4,5,6,7-Pentaacetoxy-hept-1-enyl)-4-p-tolyl-benzo[f]quinolinium; iodide 
• 75759-74-9 3-((E)-(3S,4R,5R,6R)-3,4,5,6,7-Pentaacetoxy-hept-1-enyl)-4-phenyl-benzo[f]quinolinium; iodide 
• 30469-99-9 1-C-Phenylpenta-O-acetyl-D-manno-pentit 
• 3075-41-0 2,3-Dideoxy-1-C-(p-methoxy-phenyl)-D-gluco-oct-2-en-1-ulose-pentaacetat 

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