alpha-D-Glucose pentaacetate supplier

Name
alpha-D-Glucose pentaacetate
EINECS 223-439-1
CAS No. 3891-59-6
Article Data36
CAS DataBase
Density 1.3 g/cm³
Solubility < 5 G/L (25℃)
Melting Point 109-113℃
Formula C₁₆H₂₂O₁₁
Boiling Point 434.8 °C at 760 mmHg
Molecular Weight 390.344
Flash Point 188.1 °C
Transport Information
Appearance White crystalline powder
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 2,3,4,5,6-Penta-O-acetyl-D-glucose;Penta-O-acetyl-aldehydo-D-glucose;
PSA 148.57000
LogP -0.52480

Synthetic route

: 50-99-7
D-glucose

: 108-24-7
acetic anhydride

: 3891-59-6
Penta-O-acetyl-aldehydo-D-glucose

Conditions

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;

: 4984-72-9
2,3,4,5,6-penta-O-acetyl-D-glucose diethyl dithioacetal

: 3891-59-6
Penta-O-acetyl-aldehydo-D-glucose

Conditions

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

: 3891-59-6
Penta-O-acetyl-aldehydo-D-glucose

Conditions

Conditions	Yield
With hydrogenchloride; ethanol; sodium nitrite

: penta-O-acetyl-aldehydo-D-glucose-(acetyl-formyl-hydrazone)

: 3891-59-6
Penta-O-acetyl-aldehydo-D-glucose

Conditions

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

: 108-24-7
acetic anhydride

: 84799-31-5
(Z)-6α-(β-D-glucosyloxy)-4α,5α-dihydroxy-2-cyclohexene-Δ1,α-acetonitrile

A: 3891-59-6
Penta-O-acetyl-aldehydo-D-glucose

B: Acetic acid (1S,5R,6R)-5,6-diacetoxy-2-[1-cyano-meth-(Z)-ylidene]-cyclohex-3-enyl ester

Conditions

Conditions	Yield
With pyridine; β-glucosidase Multistep reaction;

...Expand

: 122383-00-0
2-acetamido-2-deoxy-3,4,5,6-tetra-O-acetyl-D-mannose

: 3891-59-6
Penta-O-acetyl-aldehydo-D-glucose

Conditions

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

: 4984-72-9
2,3,4,5,6-penta-O-acetyl-D-glucose diethyl dithioacetal

: 7726-95-6
bromine

: 64-19-7
acetic acid

: 3891-59-6
Penta-O-acetyl-aldehydo-D-glucose

...Expand

: 7446-08-4
selenium(IV) oxide

: penta-O-acetyl-aldehydo-D-glucose-(acetyl-formyl-hydrazone)

: 108-24-7
acetic anhydride

: 64-19-7
acetic acid

: 3891-59-6
Penta-O-acetyl-aldehydo-D-glucose

...Expand

penta-O-acetyl-aldehydo-D-gluconoyl chloride: penta-O-acetyl-aldehydo-D-gluconoyl chloride

: 3891-59-6
Penta-O-acetyl-aldehydo-D-glucose

Conditions

Conditions	Yield
With Pd-BaSO4; xylene Hydrogenation;

penta-O-acetyl-aldehydo-D-glucose-ethanediylsulfanylacetal: penta-O-acetyl-aldehydo-D-glucose-ethanediylsulfanylacetal

: 3891-59-6
Penta-O-acetyl-aldehydo-D-glucose

Conditions

Conditions	Yield
With bromine; acetic acid

: 7647-01-0
hydrogenchloride

: 64-17-5
ethanol

: penta-O-acetyl-aldehydo-D-glucose oxime

sodium nitrite: sodium nitrite

: 3891-59-6
Penta-O-acetyl-aldehydo-D-glucose

...Expand

: 14131-64-7
N-acetyl-D-mannosamine

: 3891-59-6
Penta-O-acetyl-aldehydo-D-glucose

Conditions

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

: 54220-78-9, 54220-79-0, 54220-80-3
N-[(1R,2R,3S,4R)-2,3,4,5-Tetrahydroxy-1-(methoxyimino-methyl)-pentyl]-acetamide

: 3891-59-6
Penta-O-acetyl-aldehydo-D-glucose

Conditions

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

: 174761-03-6
indioside I

: 108-24-7
acetic anhydride

: 3891-59-6
Penta-O-acetyl-aldehydo-D-glucose

Conditions

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℃;

: 1365309-19-8
indioside J

: 108-24-7
acetic anhydride

: 3891-59-6
Penta-O-acetyl-aldehydo-D-glucose

Conditions

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: acidic polysaccharide AMP40S

: 108-24-7
acetic anhydride

A: 866394-64-1
D-erythritol tetraacetate

B: 3891-59-6
Penta-O-acetyl-aldehydo-D-glucose

C: 102-76-1
triacetylglycerol

D: 2,3,4,5-tetra-O-acetyl-aldehydo-L-rhamnose

Conditions

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;

...Expand

: 3891-59-6
Penta-O-acetyl-aldehydo-D-glucose

: 75-66-1
2-methylpropan-2-thiol

: 112288-76-3
Acetic acid (1S,2R,3R)-2,3,4-triacetoxy-1-((R)-1-acetoxy-2,2-bis-tert-butylsulfanyl-ethyl)-butyl ester

Conditions

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

: 3891-59-6
Penta-O-acetyl-aldehydo-D-glucose

: 1937-19-5
1-aminoguanidine hydrochloride

: 109853-93-2
C17H26N4O10*ClH

Conditions

Conditions	Yield
In water for 5h;	86%

: 3891-59-6
Penta-O-acetyl-aldehydo-D-glucose

: 572-09-8
2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

Conditions

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

: 52-90-4
L-Cysteine

: 3891-59-6
Penta-O-acetyl-aldehydo-D-glucose

: 57993-69-8, 97334-95-7, 110270-26-3, 110270-27-4, 110270-28-5
2(RS)-D-gluco-(1',2',3',4',5'-pentacetoxypentyl)thiazolidine-4(R)-carboxylic acid

Conditions

Conditions	Yield
In water	85.9%

: 3891-59-6
Penta-O-acetyl-aldehydo-D-glucose

: CH6N4*H2O*HNO3

: 109853-95-4
C17H26N4O10*HNO3

Conditions

Conditions	Yield
In water for 5h;	82%

: 3891-59-6
Penta-O-acetyl-aldehydo-D-glucose

: 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

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

: 3891-59-6
Penta-O-acetyl-aldehydo-D-glucose

: 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

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

: 3891-59-6
Penta-O-acetyl-aldehydo-D-glucose

: 52529-67-6
3-methyl-4-p-tolyl-benzo[f]quinolinium; iodide

: 75759-76-1, 75801-17-1
3-((E)-(3S,4R,5R,6R)-3,4,5,6,7-Pentaacetoxy-hept-1-enyl)-4-p-tolyl-benzo[f]quinolinium; iodide

Conditions

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

: 867296-31-9
p-hydroxycinnamoylfilicinic acid

: 3891-59-6
Penta-O-acetyl-aldehydo-D-glucose

: C40H42O15

Conditions

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%

: 3891-59-6
Penta-O-acetyl-aldehydo-D-glucose

: 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

Conditions	Yield
With pyridine	67%

: 3891-59-6
Penta-O-acetyl-aldehydo-D-glucose

: O-allylhydroxylamine trifluoroacetic acid salt

: 108-24-7
acetic anhydride

: (2R,3R,4R,5S)-6-(allyloxyimino)hexane-1,2,3,4,5-pentayl pentaacetate

Conditions

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%

...Expand

: 3891-59-6
Penta-O-acetyl-aldehydo-D-glucose

: 52529-64-3
3-methyl-4-phenylbenzoquinolinium iodide

: 75759-74-9, 75801-90-0
3-((E)-(3S,4R,5R,6R)-3,4,5,6,7-Pentaacetoxy-hept-1-enyl)-4-phenyl-benzo[f]quinolinium; iodide

Conditions

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

: 3891-59-6
Penta-O-acetyl-aldehydo-D-glucose

: 151-10-0
1,3-Dimethoxybenzene

A: 2,3,4,5,6-penta-O-acetyl-1-deoxy-1,1-bis(2,4-dimethoxyphenyl)-D-glucitol

B: 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

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

...Expand

: 3891-59-6
Penta-O-acetyl-aldehydo-D-glucose

: 108-24-7
acetic anhydride

: 10356-82-8, 118380-74-8, 17296-20-7
1,1,2,3,4,5,6-hepta-O-acetylaldehydo-D-glucose aldehydrol

Conditions

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

: 3891-59-6
Penta-O-acetyl-aldehydo-D-glucose

: 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

Conditions	Yield
With pyridine	43%

: 3891-59-6
Penta-O-acetyl-aldehydo-D-glucose

: 68-11-1
mercaptoacetic acid

: 114413-08-0, 114413-11-5, 114488-72-1, 114488-73-2
Acetic acid (1S,2R,3R)-2,3,4-triacetoxy-1-[(R)-acetoxy-(5-oxo-[1,3]oxathiolan-2-yl)-methyl]-butyl ester

Conditions

Conditions	Yield
In benzene Heating;	43%

: 3891-59-6
Penta-O-acetyl-aldehydo-D-glucose

: 107-91-5
cyanoacetic acid amide

: 120331-74-0
(2E,4E)(6R,7R)-4,6,7,8-tetraacetoxy-2-cyano-octadienamide

Conditions

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

: 3891-59-6
Penta-O-acetyl-aldehydo-D-glucose

: 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

Conditions	Yield
With pyridine	42%

: 3891-59-6
Penta-O-acetyl-aldehydo-D-glucose

: N-phenylquinaldinium perchlorate

: α-(1-phenylquinolin-2)-β--dimethine perchlorate

Conditions

Conditions	Yield
With pyridine for 1h;	40%

: 867296-31-9
p-hydroxycinnamoylfilicinic acid

: 3891-59-6
Penta-O-acetyl-aldehydo-D-glucose

: 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

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

: 3891-59-6
Penta-O-acetyl-aldehydo-D-glucose

: 1,2-dimethylquinolinium perchlorate

: 1-Methyl-2-((E)-(3S,4R,5R,6R)-3,4,5,6,7-pentaacetoxy-hept-1-enyl)-quinolinium; perchlorate

Conditions

Conditions	Yield
With pyridine	38%

: 3891-59-6
Penta-O-acetyl-aldehydo-D-glucose

: 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

Conditions	Yield
With pyridine	37%

: 3891-59-6
Penta-O-acetyl-aldehydo-D-glucose

: 123-54-6
acetylacetone

: 10399-90-3
trans-4-(D-gluco-penta-acetoxypentyl)-3-buten-2-one

Conditions

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

: 3891-59-6
Penta-O-acetyl-aldehydo-D-glucose

: 123-54-6
acetylacetone

: 83162-45-2
Acetic acid (1R,2S)-2-acetoxy-4-acetyl-5-oxo-1-((1R,2R)-1,2,3-triacetoxy-propyl)-hex-3-enyl ester

Conditions

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

: 3891-59-6
Penta-O-acetyl-aldehydo-D-glucose

: 116-54-1
dichloroacetic acid methyl ester

: 125967-07-9
methyl 2,3-anhydro-2-chloro-4,5,6,7,8-penta-O-acetyl-D-glucooctonoate

Conditions

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

: 186581-53-3, 908094-01-9
diazomethane

: 3891-59-6
Penta-O-acetyl-aldehydo-D-glucose

: 83615-60-5
1-Deoxy-3,4,5,6,7-penta-O-acetyl-L-gulo-2-heptulose

Conditions

Conditions	Yield
With methanol; diethyl ether; chloroform

: 186581-53-3, 908094-01-9
diazomethane

: 3891-59-6
Penta-O-acetyl-aldehydo-D-glucose

: 109568-68-5
penta-O-acetyl-keto-D-gluco-1,2-dideoxy-[3]octulose

Conditions

Conditions	Yield
With diethyl ether; chloroform

: 1005-39-6
4,6-diamino-2-methylthiopyrimidine

: 3891-59-6
Penta-O-acetyl-aldehydo-D-glucose

: 15470-55-0
2,5-dichlorobenzenediazonium

: O2,O3,O4,O6-tetraacetyl-D-glucose-[6-amino-5-(2,5-dichloro-phenylazo)-2-methylsulfanyl-pyrimidin-4-ylimine]

Conditions

Conditions	Yield
ueber mehrere Stufen;

...Expand

alpha-D-Glucose pentaacetate Specification

The alpha-D-Glucose pentaacetate is an organic compound with the formula C₁₆H₂₂O₁₁. The IUPAC name of this chemical is [(2R,3R,4S,5R)-2,3,4,5-tetraacetyloxy-6-oxohexyl] acetate. With the CAS registry number 3891-59-6, it is also named as 1,2,3,4,6-Penta-O-acetyl-a-D-glucopyranose.

Physical alpha-D-Glucose pentaacetate are: (1)ACD/LogP: 1.68; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 1.68; (4)ACD/LogD (pH 7.4): 1.68; (5)ACD/BCF (pH 5.5): 11.15; (6)ACD/BCF (pH 7.4): 11.15; (7)ACD/KOC (pH 5.5): 195.56; (8)ACD/KOC (pH 7.4): 195.56; (9)#H bond acceptors: 11; (10)#Freely Rotating Bonds: 11; (11)Polar Surface Area: 140.73 Å²; (12)Index of Refraction: 1.482; (13)Molar Refractivity: 85 cm³; (14)Molar Volume: 298 cm³; (15)Polarizability: 33.69×10^-24cm³; (16)Surface Tension: 46.7 dyne/cm; (17)Density: 1.3 g/cm³; (18)Flash Point: 188.1 °C; (19)Enthalpy of Vaporization: 69.09 kJ/mol; (20)Boiling Point: 434.8 °C at 760 mmHg; (21)Vapour Pressure: 9.23E-08 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C(O[C@H]1O[C@@H]([C@@H](OC(=O)C)[C@H](OC(=O)C)[C@H]1OC(=O)C)COC(=O)C)
(2)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
(3)InChIKey: LPTITAGPBXDDGR-LJIZCISZBW
(4)Std. InChI: InChI=1S/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
(5)Std. InChIKey: LPTITAGPBXDDGR-LJIZCISZSA-N

Product Name

alpha-D-Glucose pentaacetate

Synthetic route

alpha-D-Glucose pentaacetate Specification

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