2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide supplier

Name
2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide
EINECS 209-339-0
CAS No. 572-09-8
Article Data343
CAS DataBase
Density 1.49 g/cm³
Solubility decomposes in water
Melting Point 86-89 °C
Formula C₁₄H₁₉BrO₉
Boiling Point 412 °C at 760 mmHg
Molecular Weight 411.203
Flash Point 203 °C
Transport Information
Appearance white fluffy solid
Safety 24/25-36-26
Risk Codes 36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms a-D-Glucopyranosyl bromide,2,3,4,6-tetraacetate;Glucopyranosylbromide, tetraacetate, a-D- (8CI);1-Bromo-2,3,4,6-tetra(O-acetyl)-a-D-pyranoglucose;2,3,4,6-Tetra-O-acetyl-1-a-bromo-D-glucopyranose;2,3,4,6-Tetraacetyl-a-D-glucopyranosyl bromide;Acetobromo-D-glucose;Acetobromoglucose;D-Acetobromoglucose;Tetra-O-acetyl-a-D-glucopyranosylbromide;Tetra-O-acetyl-a-D-glucosyl bromide;a-Acetobromoglucose;a-D-Acetobromoglucose;
PSA 114.43000
LogP 0.46440

Synthetic route

: 604-69-3
β-D-glucose pentaacetate

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

Conditions

Conditions	Yield
With hydrogen bromide In dichloromethane Ambient temperature;	100%
With hydrogen bromide; acetic acid at 20℃; for 4h;	100%
With hydrogen bromide at 20℃; for 1.16667h;	100%

: 83-87-4, 604-68-2, 604-69-3, 2152-77-4, 4026-35-1, 4163-59-1, 4163-60-4, 4163-61-5, 4163-65-9, 4257-94-7, 4257-96-9, 16299-15-3, 19186-39-1, 19189-55-0, 25878-60-8, 25941-03-1, 32445-48-0, 32445-49-1, 32445-53-7, 32445-54-8, 34685-58-0, 34685-59-1, 43168-42-9, 43168-44-1, 43169-22-8, 43169-25-1, 66966-07-2, 70749-17-6, 80184-01-6, 93221-01-3, 93221-02-4, 99630-88-3, 109215-53-4, 115792-70-6, 115792-73-9, 139894-92-1, 139973-25-4, 144071-49-8, 147648-81-5
D-glucose pentaacetate

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

Conditions

Conditions	Yield
With hydrogen bromide; acetic acid at 20℃; Product distribution / selectivity;	100%
With hydrogen bromide; acetic acid at 20℃; for 2h;	100%
With hydrogen bromide; acetic acid In dichloromethane at 20℃; for 3h;	100%

: 604-68-2
α-D-glucopyranose peracetylate

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

Conditions

Conditions	Yield
With hydrogen bromide; acetic acid	100%
Stage #1: α-D-glucopyranose peracetylate With hydrogen bromide; acetic acid Stage #2: at 0 - 20℃; for 2h;	98%
With acetic anhydride; phosphorus tribromide In water at 0℃; for 1h;	95%

: 492-62-6
alpha-D-glucopyranose

: 506-96-7
Acetyl bromide

: 108-24-7
acetic anhydride

: 64-19-7
acetic acid

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

Conditions

Conditions	Yield
With perchloric acid In methanol at 20℃; for 2h;	99%

...Expand

: 2872-65-3, 14581-81-8, 17042-40-9, 84380-06-3, 105260-62-6
p-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

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

Conditions

Conditions	Yield
With Acetyl bromide; zinc dibromide In dichloromethane at 22℃; for 24h;	97%

: 3947-62-4, 6207-76-7, 19235-21-3, 22554-70-7, 22860-22-6, 47339-09-3, 57884-82-9, 62057-79-8, 70191-05-8, 109525-54-4, 140147-37-1, 10343-06-3
2,3,4,5-tetra-O-acetyl-D-glucopyranose

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

Conditions

Conditions	Yield
With hydrogen bromide; acetic acid In dichloromethane at 0℃; for 8h;	96%
With pyridine; (PhO)3P*Br2 In dichloromethane for 0.0833333h;	89%
With hydrogen bromide; acetic anhydride In dichloromethane at 20℃; for 4h;	85%

: 2280-44-6
D-Glucose

: 108-24-7
acetic anhydride

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

Conditions

Conditions	Yield
Stage #1: D-Glucose With Acetyl bromide In methanol Stage #2: acetic anhydride With acetic acid	95%
Stage #1: D-Glucose; acetic anhydride With perchloric acid; acetic acid at 20℃; for 0.5h; Stage #2: With Acetyl bromide In methanol for 2h;	90%
Stage #1: D-Glucose; acetic anhydride With sodium acetate at 100℃; for 5h; Stage #2: With hydrogen bromide; acetic acid In dichloromethane at 20℃; for 6h;	90%

: 492-62-6
alpha-D-glucopyranose

: 108-24-7
acetic anhydride

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

Conditions

Conditions	Yield
Stage #1: alpha-D-glucopyranose; acetic anhydride With perchloric acid at 30 - 40℃; for 1h; Stage #2: With phosphorus; bromine at 20℃; Cooling with ice; Stage #3: With water at 20℃; for 3.16667h;	90%
With hydrogen bromide; acetic acid at 20℃; for 11h;	89%
With hydrogen bromide; acetic acid at 20℃; for 11h;	85.88%

: 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

: 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

A: 4753-07-5
2,3,6,2',3',4',6'-hepta-O-acetyl-lactosyl bromide

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

C: 3068-32-4
1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

Conditions

Conditions	Yield
With Acetyl bromide; zinc dibromide In dichloromethane at 22℃; Yields of byproduct given;	A 82% B n/a C n/a

...Expand

: 231607-35-5
ethyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl disulfide

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

Conditions

Conditions	Yield
With 4 A molecular sieve; iodine(I) bromide In dichloromethane at 20℃;	82%
With iodine(I) bromide In dichloromethane at 20℃; for 0.5h;	82%

: 100432-86-8
1-deoxy-1-[(R/S)-(phenyl)sulfinyl]-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose

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

Conditions

Conditions	Yield
With N-Bromosuccinimide In tetrachloromethane Irradiation;	78%
With N-Bromosuccinimide In tetrachloromethane Product distribution; Irradiation; other glucopyranoside, other reagent, other solvent;

: C20H23NO11

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

Conditions

Conditions	Yield
With copper(ll) bromide In dichloromethane at 20℃; Molecular sieve; Inert atmosphere;	78%

: C20H28O9S

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

Conditions

Conditions	Yield
With iodine(I) bromide In dichloromethane; toluene at 20℃; for 1h; Molecular sieve; Inert atmosphere;	78%

: 3947-62-4, 6207-76-7, 19235-21-3, 22554-70-7, 22860-22-6, 47339-09-3, 57884-82-9, 62057-79-8, 70191-05-8, 109525-54-4, 140147-37-1, 10343-06-3
2,3,4,5-tetra-O-acetyl-D-glucopyranose

: 73630-93-0
1-bromo-N,N,2-trimethyl-1-propen-1-amine

A: 21678-37-5
N,N,2-trimethylpropionamide

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

Conditions

Conditions	Yield
In chloroform for 6h; Product distribution; Ambient temperature;	A n/a B 77%

...Expand

: 604-70-6
Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-methoxy-tetrahydro-pyran-4-yl ester

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

Conditions

Conditions	Yield
With acyl bromide; zinc dibromide In dichloromethane for 12h; Heating;	75%
With trimethylsilyl bromide; zinc dibromide In dichloromethane for 24h; Ambient temperature;	47%

: 4860-85-9
methyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

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

Conditions

Conditions	Yield
With acyl bromide; zinc dibromide In dichloromethane for 12h; Heating;	71%

: 100432-86-8
1-deoxy-1-[(R/S)-(phenyl)sulfinyl]-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose

A: 3947-62-4, 6207-76-7, 19235-21-3, 22554-70-7, 22860-22-6, 47339-09-3, 57884-82-9, 62057-79-8, 70191-05-8, 109525-54-4, 140147-37-1, 10343-06-3
2,3,4,5-tetra-O-acetyl-D-glucopyranose

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

Conditions

Conditions	Yield
With Bromotrichloromethane In tetrachloromethane Irradiation;	A 30% B 65%

: 2280-44-6
D-Glucose

: 506-96-7
Acetyl bromide

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

Conditions

Conditions	Yield
Stage #1: D-Glucose With perchloric acid; acetic anhydride at 30 - 40℃; for 0.5h; Stage #2: Acetyl bromide With water at 20℃; for 2h;	57.5%
With aluminum oxide In acetonitrile at 20℃; for 4h;	20%
In acetic acid for 2h; Ambient temperature;
With sulfuric acid

: 6378-65-0
n-hexyl caproate

: 604-69-3
β-D-glucose pentaacetate

A: 142-62-1
hexanoic acid

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

Conditions

Conditions	Yield
With bromine at 20℃; Irradiation; Green chemistry;	A n/a B 57%

...Expand

: 112-17-4
n-decyl acetate

: 604-69-3
β-D-glucose pentaacetate

A: 112-29-8
1-bromo dodecane

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

Conditions

Conditions	Yield
With bromine at 20℃; Irradiation; Green chemistry;	A n/a B 57%

...Expand

: 1,2,3,4,6-penta-O-acetyl-D-glucose

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

Conditions

Conditions	Yield
With hydrogen bromide; acetic acid at 20℃; for 2h;	53%

: 604-69-3
β-D-glucose pentaacetate

A: 29585-29-3
1,3,4,6-tetra-O-acetyl 2-bromo-2-deoxy-α-D-glucopyranose

B: 3947-62-4, 6207-76-7, 19235-21-3, 22554-70-7, 22860-22-6, 47339-09-3, 57884-82-9, 62057-79-8, 70191-05-8, 109525-54-4, 140147-37-1, 10343-06-3
2,3,4,5-tetra-O-acetyl-D-glucopyranose

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

Conditions

Conditions	Yield
With bromine In 2,2,4-trimethylpentane; dichloromethane at 20℃; for 7h; Irradiation; Green chemistry;	A 7% B 15% C 22%

...Expand

: 1138026-28-4
2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-1-C-sulfonamide

A: 2,3,4,6-tetra-O-acetyl-1-C-bromo-β-D-glucopyranosyl-1-C-sulfonamide

B: 2,3,4,6-tetra-O-acetyl-5-C-bromo-β-D-glucopyranosyl-1-C-sulfonamide

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

Conditions

Conditions	Yield
With bromine; potassium carbonate In α,α,α-trifluorotoluene for 4h; Reflux; Heat lamp;	A 12% B 12% C 19%

...Expand

: 604-69-3
β-D-glucose pentaacetate

A: 69534-61-8
1,2,3,4,6-Penta-O-acetyl-5-bromo-β-D-glucopyranose

B: 75868-36-9
2,3,4,6-tetra-O-acetyl-1-bromo-D-glucopyranosyl bromide

C: 75860-51-4
2,3,4,6-tetra-O-acetyl-5-bromo-β-D-glucopyranosyl bromide

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

Conditions

Conditions	Yield
With bromine In tetrachloromethane for 3h; Heating; Irradiation;	A n/a B n/a C 13% D 0.06 g
With bromine In tetrachloromethane for 3h; Heating; Irradiation; Yield given;	A n/a B n/a C 13% D 0.06 g
With bromine In tetrachloromethane for 3h; Heating; Irradiation; Yields of byproduct given;	A n/a B n/a C 13% D 0.06 g

...Expand

: 604-69-3
β-D-glucose pentaacetate

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

B: 604-68-2
α-D-glucopyranose peracetylate

Conditions

Conditions	Yield
With bromine In ethyl acetate at 20℃; for 19h; Irradiation; Darkness; Green chemistry;	A 8% B n/a

: 50-99-7
D-glucose

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

Conditions

Conditions	Yield
With Acetyl bromide; acetic acid
Multi-step reaction with 2 steps 1.1: pyridine / 1 h / 0 - 20 °C / Inert atmosphere 1.2: 6 h / 20 °C / Inert atmosphere 2.1: hydrogen bromide; acetic acid / dichloromethane / 1 h / Cooling with ice View Scheme
Multi-step reaction with 2 steps 1: pyridine / 6 h / 0 °C 2: acetic acid; hydrogen bromide / dichloromethane / 2 h View Scheme

: 50-99-7
D-glucose

: 108-24-7
acetic anhydride

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

Conditions

Conditions	Yield
With perchloric acid anschl. mit Phosphor, Brom und H2O;
With pyridine; hydrogen bromide; acetic acid Yield given; Multistep reaction;
Stage #1: D-glucose; acetic anhydride With iodine at 20℃; for 1h; Stage #2: With hydrogen bromide; acetic acid
Stage #1: D-glucose; acetic anhydride With perchloric acid In water at 40℃; for 1h; Stage #2: With phosphorus; bromine In water at 0 - 20℃; for 4h;

: 77938-63-7
sodium chloride * 2 d-glucose * H2O

: 108-24-7
acetic anhydride

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

Conditions

Conditions	Yield
With sulfuric acid anschl. Behandeln des von der gebildeten Essigsaeure befreiten Rktprod. mit HBr;

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

: 13992-25-1
1-azido-1-deoxy-β-D-glucopyranoside tetraacetate

Conditions

Conditions	Yield
With tetramethylguanidinum azide In nitromethane at 25℃; for 2.5h;	100%
With sodium azide In N,N-dimethyl-formamide for 48h; Inert atmosphere;	100%
With N,N,N',N'-tetramethylguanidinium azide In dichloromethane for 2h; Ambient temperature; other glycosyl halides;	99%

: 592-87-0
lead(II) thiocyanate

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

: 14152-97-7
2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate

Conditions

Conditions	Yield
In benzene for 6h; Heating;	100%
In 5,5-dimethyl-1,3-cyclohexadiene at 130 - 140℃; for 0.416667h; Microwave irradiation;	89.66%
In toluene for 4h; Reflux;	89%

: 17356-08-0
thiourea

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

: 40591-65-9
2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiouronium bromide

Conditions

Conditions	Yield
In acetone at 60℃; Inert atmosphere; Reflux;	100%
In acetone for 0.5h; Heating;	95%
In acetone for 0.05h; microwave irradiation;	90%

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

: 165053-19-0
3,4,6-tri-O-acetyl-1,2-O-vinylidene-α-D-glucopyranose

Conditions

Conditions	Yield
With silver perchlorate; N-ethyl-N,N-diisopropylamine In benzene at 20℃; for 1h; Molecular sieve; Inert atmosphere; Darkness;	100%
With N-ethyl-N,N-diisopropylamine; silver(l) oxide In benzene for 6h; Heating;

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

: 724733-04-4
4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoro-undecanoic acid (4-mercapto-phenyl)-methyl-amide

: Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{4-[(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoro-undecanoyl)-methyl-amino]-phenylsulfanyl}-tetrahydro-pyran-3-yl ester

Conditions

Conditions	Yield
With sodium carbonate In water; ethyl acetate at 20℃; for 2h;	100%

: CDP-Star enol ether phenol

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

: glucon-Star enol ether tetraacetate

Conditions

Conditions	Yield
With tetrabutylammomium bromide; sodium hydroxide; phase transfer catalyst In dichloromethane at 20℃; for 0.5h;	100%

: 612-25-9
2-Nitrobenzyl alcohol

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

: 34546-55-9
2-nitrobenzyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

Conditions

Conditions	Yield
With iodine; silver carbonate In dichloromethane at 20℃; for 16h; Molecular sieve; Inert atmosphere;	100%
With iodine; 2,3-dicyano-5,6-dichloro-p-benzoquinone In acetonitrile for 4h; Molecular sieve; Inert atmosphere;	91%

: C22H24N2O6

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

: C36H42N2O15

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 80℃;	100%

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

: 3947-62-4, 6207-76-7, 19235-21-3, 22554-70-7, 22860-22-6, 47339-09-3, 57884-82-9, 62057-79-8, 70191-05-8, 109525-54-4, 140147-37-1, 10343-06-3
2,3,4,5-tetra-O-acetyl-D-glucopyranose

Conditions

Conditions	Yield
With water; silver carbonate In acetone for 0.5h;	99%
With N-methylacridinium iodide; sodium cyanoborohydride In N,N-dimethyl-formamide for 1h; Reagent/catalyst; Solvent; UV-irradiation;	55.8%
With acetone; silver carbonate

: 77-52-1
ursolic acid

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

: 16684-20-1
2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl 3β-hydroxyurs-12-en-28-oate

Conditions

Conditions	Yield
With tetrabutylammomium bromide; potassium carbonate In dichloromethane; water for 8h; Heating;	99%
With Aliquat 336; potassium carbonate In dichloromethane; water for 48h; Ambient temperature;	95%
With potassium carbonate In N,N-dimethyl-formamide at 20℃;	90%

: 65-85-0
benzoic acid

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

: 38430-69-2
O2,O3,O4,O6-Tetraacetyl-O1-benzoyl-β-D-glucopyranose

Conditions

Conditions	Yield
With tetraethylammonium bromide; potassium carbonate In dichloromethane at 20℃; Reagent/catalyst; Molecular sieve;	99%
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 24h; Molecular sieve; Inert atmosphere;	84%
With Amberlyst A-26 hydroxide form 1.) hexane, 2.) benzene, reflux, 12 h;	65%

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

: 93-09-4
naphthalene-2-carboxylate

: 1-O-(2-naphthoyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose

Conditions

Conditions	Yield
With tetraethylammonium bromide; potassium carbonate In dichloromethane at 20℃; Molecular sieve;	99%
With Aliquat 336; potassium carbonate In dichloromethane; water Ambient temperature;	96%

: 148-18-5
sodium N,N-diethyldithiocarbamate

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

: S-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl) N,N-diethyldithiocarbamate

Conditions

Conditions	Yield
In acetone for 1h; Reflux;	99%
In acetonitrile at 25℃; for 1h;	63%

: 149-30-4
2-thioxo-3H-1,3-benzothiazole

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

: 6067-32-9, 6426-38-6
2-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosylmercapto)1,3-benzothiazole

Conditions

Conditions	Yield
With potassium hydroxide In acetonitrile at 20℃; for 1h;	99%

: 1095998-03-0
4-(pyridin-2'-yl)thiazole-2(3H)-thione sodium salt

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

: 1095998-22-3
4-(pyridine-2-yl)-thiazole-2-yl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside

Conditions

Conditions	Yield
In acetonitrile at 20℃; for 8h; Inert atmosphere;	99%

: 74247-81-7
6-O-tert-butyldimethylsilanyl-1-O-methyl-α-D-mannopyranoside

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

: 1330004-16-4
methyl 6-O-tert-butyldimethylsilyl-3-O-(2′,3′,4′,6′-tetra-O-acetyl-β-D-glucopyranosyl)-α-D-mannopyranoside

Conditions

Conditions	Yield
With diphenylborate ethanolamine ester; silver(l) oxide In acetonitrile at 23℃; for 16h; Kinetics; Mechanism; Concentration; Reagent/catalyst; Koenigs-Knorr synthesis; Inert atmosphere; regioselective reaction;	99%
With [2-(1-methyl-1H-imidazol-2-yl)phenyl]boronic acid; silver(l) oxide In acetonitrile at 30℃; for 24h; Reagent/catalyst; Koenigs-Knorr Glycosidation; Inert atmosphere; regioselective reaction;	98%

: 181480-80-8
6-O-tert-butyldimethylsilanyl-1-O-methyl-α-D-galactopyranoside

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

: 1330004-23-3
methyl 6-O-tert-butyldimethylsilyl-3-O-(2’,3’,4’,6’-tetra-O-acetyl-β-D-glucopyranosyl)-α-D-galactopyranoside

Conditions

Conditions	Yield
With [2-(1-methyl-1H-imidazol-2-yl)phenyl]boronic acid; silver(l) oxide In acetonitrile at 30℃; for 24h; Koenigs-Knorr Glycosidation; Inert atmosphere; regioselective reaction;	99%
With diphenylborate ethanolamine ester; silver(l) oxide In acetonitrile at 23℃; for 16h; Koenigs-Knorr synthesis; Inert atmosphere; regioselective reaction;	74%
With diphenylborate ethanolamine ester; silver(l) oxide In acetonitrile at 23℃; for 16h; Reagent/catalyst; regioselective reaction;	74%

: 617-04-9
(2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol

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

: methyl 3-O-(2’,3’,4’,6’-tetra-O-acetyl-β-D-glucopyranosyl)-α-D-mannopyranoside

Conditions

Conditions	Yield
Stage #1: (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol With diphenyltin(IV) dichloride In acetonitrile at 20℃; for 0.166667h; Stage #2: 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide With 5,5'-dimethyl-2,2'-bipyridine; silver(l) oxide In acetonitrile at 20 - 35℃; for 24h; Reagent/catalyst; Koenigs-Knorr Glycosidation; stereoselective reaction;	99%

: 585-76-2
m-bromobenzoic acid

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

: 1-O-(3-bromobenzoyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose

Conditions

Conditions	Yield
With tetraethylammonium bromide; potassium carbonate In dichloromethane at 20℃; Molecular sieve;	99%

: 503-74-2
3-methylbutyric acid

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

: 1-O-(3-methylbutanoyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose

Conditions

Conditions	Yield
With tetraethylammonium bromide; potassium carbonate In dichloromethane at 20℃; Molecular sieve;	99%

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

: 1759-53-1
cyclopropanecarboxylic acid

: 1-O-(cyclopropanecarbonyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose

Conditions

Conditions	Yield
With tetraethylammonium bromide; potassium carbonate In dichloromethane at 20℃; Molecular sieve;	99%

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

: 10387-40-3
potassium thioacetate

: 6806-56-0, 13639-50-4, 51898-27-2, 62860-10-0, 63783-77-7, 92217-67-9, 92217-68-0, 130796-15-5
O2,O3,O4,O6,S-Pentaacetyl-1-thio-β-D-glucopyranose

Conditions

Conditions	Yield
for 2h; Neat (no solvent); Ball milling;	98%
In acetone at 20℃; for 8h;	88%
In acetone at 20℃;	86%

: 107-18-6
allyl alcohol

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

: 10343-15-4, 39698-55-0, 54400-76-9, 78730-32-2, 119111-31-8, 119111-32-9
Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-allyloxy-tetrahydro-pyran-4-yl ester

Conditions

Conditions	Yield
With copper(II) sulfate; mercury dibromide; mercury(II) oxide In chloroform at 0 - 20℃; for 10h;	98%
With indium(III) chloride; 4 A molecular sieve In dichloromethane at 0 - 3℃; for 72h;	86%
With metal carbonates In neat (no solvent) for 2.5h; Milling;	82%

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

: 13137-69-4
1-deoxy-D-glucose tetraacetate

Conditions

Conditions	Yield
With -butyl vinyl ether	98%
With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride In benzene at 80℃; for 1h;	97%
With 2,2'-azobis(isobutyronitrile); phenylsilane for 1.16667h; Heating;	90%

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

: 439-03-2, 439-04-3, 439-05-4, 2823-44-1, 2823-46-3, 3934-29-0, 4163-44-4, 4163-45-5, 20409-31-8, 23235-96-3, 51897-75-7, 51897-76-8, 51897-77-9, 57573-38-3, 62561-28-8, 126641-47-2
2-(acetoxymethyl)-6-fluorotetrahydro-2H-pyran-3,4,5-triyl triacetate

Conditions

Conditions	Yield
With silver fluoride In acetonitrile at 20℃; Inert atmosphere; Darkness;	98%
With triethylamine tris(hydrogen fluoride) In tetrachloromethane for 2h; Heating;	83%
With (trifluoromethyl)zinc chloride; 3 A molecular sieve In dichloromethane for 12h; Ambient temperature;	83%
With potassium hydrogen bifluoride In acetonitrile for 24h; Heating;	70%
With silver fluoride; acetonitrile

: 4064-06-6
1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

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

: 66964-24-7
3,4,6-Tri-O-acetyl-1,2-O-<1-(exo-1,2:3,4-di-O-isopropylidene-α-D-galacatopyranose-6-yl)ethylidene>-α-D-glucopyranose

Conditions

Conditions	Yield
With silver imidazolate; mercury dichloride In dichloromethane for 24h; 3 Angstroem molecular sieves;	98%
With 4 A molecular sieve; tetrabutylammomium bromide; N-ethyl-N,N-diisopropylamine In dichloromethane at 40℃; under 6000480 Torr; for 20h; Yield given;

2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide Chemical Properties

Product Name: Acetobromglucose (CAS NO.572-09-8)

Molecular Formula: C₁₄H₁₉BrO₉
Molecular Weight: 411.20g/mol
Mol File: 572-09-8.mol
EINECS: 209-339-0
Appearance: White powder
Melting Point: 83-88 ºC
Boiling point: 412 °C at 760 mmHg
Flash Point: 203 °C
Density: 1.49 g/cm³
Water Solubility: Decomposes
Surface Tension: 47.9 dyne/cm
Enthalpy of Vaporization: 66.46 kJ/mol
Vapour Pressure: 5.35E-07 mmHg at 25°C
XLogP3-AA: 1.5
H-Bond Donor: 0
H-Bond Acceptor: 9
Structure Descriptors of Acetobromglucose (CAS NO.572-09-8):
IUPAC Name: [(2R,3R,4S,5R,6R)-4,5-diacetyloxy-2-(acetyloxymethyl)-6-bromooxan-3-yl]acetate
Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)Br)OC(=O)C)OC(=O)C)OC(=O)C
Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)Br)OC(=O)C)OC(=O)C)OC(=O)C
InChI: InChI=1S/C14H19BrO9/c1-6(16)20-5-10-11(21-7(2)17)12(22-8(3)18)13(14(15)24-10)23-9(4)19/h10-14H,5H2,1-4H3/t10-,11-,12+,13-,14+/m1/s1
InChIKey: CYAYKKUWALRRPA-RGDJUOJXSA-N

2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide Safety Profile

Safety Information of Acetobromglucose (CAS NO.572-09-8):
Safety Statements: S24/25
24: Avoid contact with skin
25: Avoid contact with eyes

2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide Specification

Acetobromglucose , its CAS NO. is 572-09-8, the synonyms are EINECS 209-339-0 ; 2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide ; alpha-D-Glucopyranosyl bromide, tetraacetate .

Product Name

2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide

Synthetic route

2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide Chemical Properties

2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide Safety Profile

2,3,4,6-Tetra-O-acetyl-alpha-D-glucopyranosyl bromide Specification

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