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67546-20-7

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Basic Information
CAS No.: 67546-20-7
Name: 1,6-Anhydro-2-azido-2-deoxy-β-D-glucopyranose
Article Data: 9
Molecular Structure:
Molecular Structure of 67546-20-7 (1,6-Anhydro-2-azido-2-deoxy-β-D-glucopyranose)
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
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1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose

Conditions
ConditionsYield
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%
139437-39-1

1,6-anhydro-2-deoxy-2-iodo-β-D-glucopyranose

67546-20-7

1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose

Conditions
ConditionsYield
With sodium azide In water; N,N-dimethyl-formamide at 120℃; for 2h;81%
With sodium azide In water; N,N-dimethyl-formamide75%
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;
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3,4-Di-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose

67546-20-7

1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose

Conditions
ConditionsYield
With sodium methylate In methanol Ambient temperature;
13265-84-4

D-glucal

67546-20-7

1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose

Conditions
ConditionsYield
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;

Trifluoro-methanesulfonic acid (1R,2S,3S,4S,5R)-2,3-dihydroxy-6,8-dioxa-bicyclo[3.2.1]oct-4-yl ester

67546-20-7

1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose

Conditions
ConditionsYield
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

Acetic acid (1R,2R,3S,4S,5R)-2-acetoxy-4-trifluoromethanesulfonyloxy-6,8-dioxa-bicyclo[3.2.1]oct-3-yl ester

67546-20-7

1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaN3 / dimethylformamide / 2 h / Ambient temperature
2: sodium methoxide / methanol / Ambient temperature
View Scheme
14168-65-1

mannosan

67546-20-7

1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose

Conditions
ConditionsYield
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
604-68-2

α-D-glucopyranose peracetylate

67546-20-7

1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose

Conditions
ConditionsYield
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

sodium azide

139437-39-1

1,6-anhydro-2-deoxy-2-iodo-β-D-glucopyranose

67546-20-7

1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose

Conditions
ConditionsYield
With sodium hydrogencarbonate In N,N-dimethyl-formamide at 20 - 122℃; Industry scale;
492-62-6

alpha-D-glucopyranose

67546-20-7

1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose

Conditions
ConditionsYield
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
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