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CAS No.: | 67546-20-7 |
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Name: | 1,6-Anhydro-2-azido-2-deoxy-β-D-glucopyranose |
Article Data: | 9 |
Molecular Structure: | |
Formula: | C6H9N3O4 |
Molecular Weight: | 187.155 |
Synonyms: | 1,6-ANHYDRO-2-AZIDO-2-DEOXY-B-D-GLUCOPYRANOSE;1,6-ANHYDRO-2-AZIDO-2-DEOXY-SS-D-GLUCOPYRANOSE;1,6-ANHYDRO-2-AZIDO-2-DEOXY-BETA-D-GLUCOPYRANOSE; |
PSA: | 108.67000 |
LogP: | -1.40504 |
1,6:2,3-dianhydro-β-D-mannopyranose
1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose
Conditions | Yield |
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With sodium azide; ammonium chloride In methanol; water for 108h; Heating; | 95% |
With aluminum oxide; lithium azide In N,N-dimethyl-formamide; toluene microwave irradiation; | 85% |
With sodium azide; ammonium chloride In methanol; water for 108h; Heating / reflux; | 66.5% |
1,6-anhydro-2-deoxy-2-iodo-β-D-glucopyranose
1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose
Conditions | Yield |
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With sodium azide In water; N,N-dimethyl-formamide at 120℃; for 2h; | 81% |
With sodium azide In water; N,N-dimethyl-formamide | 75% |
With sodium azide In water; N,N-dimethyl-formamide Heating; | |
Multi-step reaction with 2 steps 1: 95 percent / NaHCO3 / dimethylformamide; H2O / 4 h / 120 °C 2: 95 percent / sodium azide; ammonium chloride / methanol; H2O / 108 h / Heating View Scheme | |
With sodium azide In water; N,N-dimethyl-formamide Reflux; |
3,4-Di-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose
1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose
Conditions | Yield |
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With sodium methylate In methanol Ambient temperature; |
D-glucal
1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose
Conditions | Yield |
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Multi-step reaction with 2 steps 1.1: (Bu3Sn)2O; 3 Angstroem MS / acetonitrile / 3 h / Heating 1.2: 65 percent / I2 / CH2Cl2 / 0.25 h / 0 °C 2.1: NaN3 / H2O; dimethylformamide / Heating View Scheme | |
Multi-step reaction with 2 steps 1: 1) (Bu3Sn)2O, molecular sieves (3 Angstroem), 2) I2 / 1) MeCN, reflux, 3 h, 2) r.t., 1.5 h 2: 81 percent / NaN3 / dimethylformamide; H2O / 2 h / 120 °C View Scheme | |
Stage #1: D-glucal With bis(tri-n-butyltin)oxide In acetonitrile for 3h; Molecular sieve; Reflux; Stage #2: With iodine at 20℃; for 1.5h; Stage #3: With sodium azide In water; N,N-dimethyl-formamide at 120℃; for 3h; |
1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose
Conditions | Yield |
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Multi-step reaction with 3 steps 1: pyridine / toluene; dimethylformamide; CH2Cl2 / 1.5 h / -10 - 0 °C 2: NaN3 / dimethylformamide / 2 h / Ambient temperature 3: sodium methoxide / methanol / Ambient temperature View Scheme |
1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose
Conditions | Yield |
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Multi-step reaction with 2 steps 1: NaN3 / dimethylformamide / 2 h / Ambient temperature 2: sodium methoxide / methanol / Ambient temperature View Scheme |
mannosan
1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose
Conditions | Yield |
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Multi-step reaction with 4 steps 1: 1.) Bu2SnO / 1.) toluene, DMF, 2.) CH2Cl2, -10 deg C, 1.5 h 2: pyridine / toluene; dimethylformamide; CH2Cl2 / 1.5 h / -10 - 0 °C 3: NaN3 / dimethylformamide / 2 h / Ambient temperature 4: sodium methoxide / methanol / Ambient temperature View Scheme |
α-D-glucopyranose peracetylate
1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose
Conditions | Yield |
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Multi-step reaction with 3 steps 1.1: hydrogen bromide; acetic acid / 2 h / 20 °C / Industry scale 1.2: 2 h / 0 - 5 °C / Industry scale 2.1: sodium methylate / methanol / 5 - 20 °C / pH 9 - 9.5 / Industry scale 2.2: 5 h / Reflux; Molecular sieve; Industry scale 2.3: 0 - 20 °C 3.1: sodium hydrogencarbonate / N,N-dimethyl-formamide / 20 - 122 °C / Industry scale View Scheme |
1,6-anhydro-2-deoxy-2-iodo-β-D-glucopyranose
1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose
Conditions | Yield |
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With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20 - 122℃; Industry scale; |
alpha-D-glucopyranose
1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose
Conditions | Yield |
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Multi-step reaction with 4 steps 1.1: sulfuric acid; acetic acid / 2.5 h / 0 - 75 °C / Industry scale 2.1: hydrogen bromide; acetic acid / 2 h / 20 °C / Industry scale 2.2: 2 h / 0 - 5 °C / Industry scale 3.1: sodium methylate / methanol / 5 - 20 °C / pH 9 - 9.5 / Industry scale 3.2: 5 h / Reflux; Molecular sieve; Industry scale 3.3: 0 - 20 °C 4.1: sodium hydrogencarbonate / N,N-dimethyl-formamide / 20 - 122 °C / Industry scale View Scheme |