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81058-27-7

Basic Information
CAS No.: 81058-27-7
Name: 2,3,4,6-Tetra-O-pivaloyl-alpha-D-glucopyranosyl bromide
Article Data: 9
Molecular Structure:
Molecular Structure of 81058-27-7 (2,3,4,6-Tetra-O-pivaloyl-alpha-D-glucopyranosyl bromide)
Formula: C26H43BrO9
Molecular Weight: 579.526
Synonyms: 2,3,4,6-Tetra-O-Pivaloyl-α-D-Glucopyranosyl Bromide;
EINECS: 686-241-8
Density: 1.22g/cm3
Boiling Point: 530.5oC at 760 mmHg
Flash Point: 274.6oC
Hazard Symbols: Xi
Risk Codes: 36/37/38
Safety: 26-36
PSA: 114.43000
LogP: 4.56920
Synthetic route
81058-26-6

1,2,3,4,6-penta-O-trimethylacetyl-β-D-glucopyranose

81058-27-7

2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide

Conditions
ConditionsYield
With bismuth(III) bromide; trimethylsilyl bromide In dichloromethane at 20℃; for 24h;97%
With hydrogen bromide In dichloromethane; acetic acid for 12h;64%
With hydrogen bromide; acetic acid In dichloromethane at 5℃; for 12h;63%
1213234-53-7

1,2,3,4,6-penta-O-pivaloyl-D-glucopyranoside

81058-27-7

2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide

Conditions
ConditionsYield
With trimethylsilyl bromide; zinc dibromide In dichloromethane at 10 - 25℃; Temperature; Inert atmosphere;83%
Stage #1: 1,2,3,4,6-penta-O-pivaloyl-D-glucopyranoside With zinc dibromide In dichloromethane at 20℃; for 0.166667h; Inert atmosphere;
Stage #2: With sodium hydrogencarbonate In dichloromethane; water
Stage #1: 1,2,3,4,6-penta-O-pivaloyl-D-glucopyranoside With trimethylsilyl bromide; zinc dibromide In dichloromethane at 20℃; for 24h; Inert atmosphere;
Stage #2: With sodium hydrogencarbonate In dichloromethane; water at 0℃; pH=7 - 8;
114179-84-9

1,2,3,4,6-penta-O-pivaloyl-D-glucopyranoside

81058-27-7

2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide

Conditions
ConditionsYield
With hydrogen bromide; acetic acid In dichloromethane at 0 - 20℃; for 3h;70%
With hydrogen bromide; acetic acid In dichloromethane Molecular sieve;
3282-30-2

pivaloyl chloride

81058-27-7

2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 73 percent / Et3N; DMAP / CH2Cl2 / 24 h / 20 °C
2: 97 percent / BiBr3; Me3SiBr / CH2Cl2 / 24 h / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: 74 percent / pyridine / CHCl3 / 120 h / Ambient temperature
2: 64 percent / 40percent HBr / CH2Cl2; acetic acid / 12 h
View Scheme
Multi-step reaction with 2 steps
1: triethylamine / dmap / dichloromethane / 0.75 h / 20 °C / Inert atmosphere
2: zinc dibromide / dichloromethane / 0.17 h / 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1.1: triethylamine / dmap / dichloromethane / 20.5 h / 0 - 20 °C / Inert atmosphere
2.1: trimethylsilyl bromide / zinc dibromide / dichloromethane / 24 h / 20 °C / Inert atmosphere
2.2: 0 °C / pH 7 - 8
View Scheme
Multi-step reaction with 2 steps
1: pyridine; dmap; thionyl chloride / dichloromethane / 2 h / 48 - 50 °C / Reflux; Large scale
2: zinc dibromide; trimethylsilyl bromide / dichloromethane / 10 - 25 °C / Inert atmosphere
View Scheme
492-62-6

alpha-D-glucopyranose

81058-27-7

2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: triethylamine / dmap / dichloromethane / 20.5 h / 0 - 20 °C / Inert atmosphere
2.1: trimethylsilyl bromide / zinc dibromide / dichloromethane / 24 h / 20 °C / Inert atmosphere
2.2: 0 °C / pH 7 - 8
View Scheme
Multi-step reaction with 2 steps
1: pyridine; dmap; thionyl chloride / dichloromethane / 2 h / 48 - 50 °C / Reflux; Large scale
2: zinc dibromide; trimethylsilyl bromide / dichloromethane / 10 - 25 °C / Inert atmosphere
View Scheme
3282-30-2

pivaloyl chloride

81058-27-7

2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide

Conditions
ConditionsYield
In dichloromethane
50-99-7

D-glucose

2857-97-8

trimethylsilyl bromide

A

81058-27-7

2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide

B

3282-30-2

pivaloyl chloride

Conditions
ConditionsYield
In dichloromethane
In dichloromethane
In dichloromethane
97-30-3

methyl-alpha-D-glucopyranoside

A

81058-27-7

2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide

B

3282-30-2

pivaloyl chloride

Conditions
ConditionsYield
With sodium bromide In dichloromethane
50-99-7

D-glucose

A

81058-27-7

2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide

B

3282-30-2

pivaloyl chloride

Conditions
ConditionsYield
With sodium bromide In dichloromethane
112-72-1

1-Tetradecanol

81058-27-7

2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide

225641-98-5

tetradecyl 2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranoside

Conditions
ConditionsYield
With silver carbonate In diethyl ether97%
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Specification

The 2,3,4,6-Tetra-O-pivaloyl-alpha-D-glucopyranosyl bromide is an organic compound with the formula C26H43BrO9. The IUPAC name of this chemical is . With the CAS registry number 81058-27-7, it is also named as 2,3,4,6-Tetrakis-O-(2,2-dimethylpropanoyl)-α-L-altropyranosyl bromide and α-L-altropyranosyl bromide, tetrakis(2,2-dimethylpropanoate).

Physical properties about this chemical are: (1)ACD/LogP:  6.96; (2)# of Rule of 5 Violations:  2; (3)6.96  ACD/LogD (pH 7.4):  6.96; (4)#H bond acceptors:  9; (5)#H bond donors:  0; (6)#Freely Rotating Bonds:  13; (7)Index of Refraction:  1.494; (8)Molar Refractivity:  137.2 cm3; (9)Molar Volume:  471.1 cm3; (10)Surface Tension:  41 dyne/cm; (11)Density:  1.22 g/cm3; (12)Flash Point:  274.6 °C; (13)Enthalpy of Vaporization:  80.58 kJ/mol; (14)Boiling Point:  530.5 °C at 760 mmHg; (15)Vapour Pressure:  2.45E-11 mmHg at 25°C.