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CAS No.: | 81058-27-7 |
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Name: | 2,3,4,6-Tetra-O-pivaloyl-alpha-D-glucopyranosyl bromide |
Article Data: | 9 |
Molecular Structure: | |
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 |
1,2,3,4,6-penta-O-trimethylacetyl-β-D-glucopyranose
2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide
Conditions | Yield |
---|---|
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% |
1,2,3,4,6-penta-O-pivaloyl-D-glucopyranoside
2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide
Conditions | Yield |
---|---|
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; |
1,2,3,4,6-penta-O-pivaloyl-D-glucopyranoside
2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide
Conditions | Yield |
---|---|
With hydrogen bromide; acetic acid In dichloromethane at 0 - 20℃; for 3h; | 70% |
With hydrogen bromide; acetic acid In dichloromethane Molecular sieve; |
pivaloyl chloride
2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide
Conditions | Yield |
---|---|
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 |
alpha-D-glucopyranose
2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide
Conditions | Yield |
---|---|
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 |
Conditions | Yield |
---|---|
In dichloromethane |
D-glucose
trimethylsilyl bromide
A
2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide
B
pivaloyl chloride
Conditions | Yield |
---|---|
In dichloromethane | |
In dichloromethane | |
In dichloromethane |
methyl-alpha-D-glucopyranoside
A
2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide
B
pivaloyl chloride
Conditions | Yield |
---|---|
With sodium bromide In dichloromethane |
D-glucose
A
2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide
B
pivaloyl chloride
Conditions | Yield |
---|---|
With sodium bromide In dichloromethane |
1-Tetradecanol
2,3,4,6-tetra-O-pivaloyl-α-D-glucopyranosyl bromide
tetradecyl 2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranoside
Conditions | Yield |
---|---|
With silver carbonate In diethyl ether | 97% |
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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.