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CAS No.: | 68733-20-0 |
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Name: | 1,3,4,6-TETRA-O-ACETYL-2-AZIDO-2-DEOXY-ALPHA-D-MANNOPYRANOSE |
Article Data: | 14 |
Molecular Structure: | |
Formula: | C14H19 N3 O9 |
Molecular Weight: | 373.32 |
Synonyms: | [(2R,3S,4R,5S,6R)-3,4,6-triacetyloxy-5-azidooxan-2-yl]methyl acetate; |
Melting Point: | 132 °C |
PSA: | 164.18000 |
LogP: | -0.16744 |
acetic anhydride
methyl 3-O-acetyl-2-azido-4,6-O-benzylidene-2-deoxy-α-D-mannopyranoside
1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-D-mannopyranoside
Conditions | Yield |
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With sulfuric acid at 0℃; for 1h; | 92% |
acetic anhydride
1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-D-mannopyranoside
Conditions | Yield |
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With sulfuric acid at 20℃; for 2h; | 82% |
acetic anhydride
Methyl 2-azido-2-deoxy-4,6-O-(phenylmethylene)-α-D-mannopyranoside
1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-D-mannopyranoside
Conditions | Yield |
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With sulfuric acid at 20℃; for 2.5h; | 78% |
With sulfuric acid at 20℃; for 0.666667h; | 75% |
mercury(II) diacetate
D-glucal triacetate
A
2-azido-2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranosyl acetate
B
1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-β-D-glucopyranose
D
1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-D-mannopyranoside
Conditions | Yield |
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With chlorine azide In tetrachloromethane at 0℃; for 1h; Product distribution; Irradiation; other halogen-azide, in other solvents under irradiation or in the dark, various time and temperature; | A 9% B 62% C 8% D 11% |
With chlorine azide 1.) CCl4, irrad., 0 deg C, 1 h; 2.) glacial acetic acid, room temp.; Yield given. Multistep reaction; | A n/a B 62% C 8% D 11% |
With chlorine azide 1.) CCl4, irrad., 0 deg C, 1 h; 2.) glacial acetic acid, room temp.; Yield given. Multistep reaction; | A 9% B 62% C 8% D n/a |
With chlorine azide 1.) CCl4, irrad., 0 deg C, 1 h, 2.) glacial acetic acid, room temp.; Yield given. Multistep reaction; | A 9% B n/a C 8% D 11% |
1,3,4,6-tetra-O-acetyl-2-O-trifluoromethanesulfonyl-α-D-glucopyranose
1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-D-mannopyranoside
Conditions | Yield |
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With sodium azide In N,N-dimethyl-formamide at 60℃; for 0.5h; | 58% |
With sodium azide In N,N-dimethyl-formamide | 20% |
With sodium azide In N,N-dimethyl-formamide at 60℃; for 5h; | 10% |
sodium acetate
Acetic acid (2R,3S,4R)-4-acetoxy-2-acetoxymethyl-5-azido-6-nitrooxy-tetrahydro-pyran-3-yl ester
A
2-azido-2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranosyl acetate
B
1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-β-D-glucopyranose
C
1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-D-mannopyranoside
Conditions | Yield |
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In acetic acid at 100℃; for 1h; | A n/a B n/a C 17% |
sodium acetate
D-glucal triacetate
A
2-azido-2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranosyl acetate
B
1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-D-mannopyranoside
Conditions | Yield |
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With sodium azide; ammonium cerium(IV) nitrate 1.) EtOAc, CH3CN, -40 deg C, 6 d; 2.) glacial acetic acid, 100 deg C, 1 h; Yield given. Multistep reaction. Yields of byproduct given; |
sodium acetate
D-glucal triacetate
1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-D-mannopyranoside
Conditions | Yield |
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With sodium azide; ammonium cerium(IV) nitrate 1.) acetonitrile, ethylacetate, -40 deg C; Yield given. Multistep reaction; |
1,3,4,6-tetra-O-acetyl glucopyranose
1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-D-mannopyranoside
Conditions | Yield |
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Multi-step reaction with 2 steps 1: 97 percent / pyridine / CH2Cl2 / 1 h / -20 °C 2: 58 percent / NaN3 / dimethylformamide / 0.5 h / 60 °C View Scheme | |
Multi-step reaction with 2 steps 1: 66 percent / pyridine; CH2Cl2 / 1.5 h / 3 °C 2: 10 percent / NaN3 / dimethylformamide / 5 h / 60 °C View Scheme |
methyl 4,6-O-benzylidene-α-D-glucopyranoside
1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-D-mannopyranoside
Conditions | Yield |
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Multi-step reaction with 3 steps 1: pyridine / dichloromethane / 3 h / -78 - 20 °C 2: sodium azide / N,N-dimethyl-formamide / 2 h / 80 °C 3: sulfuric acid / 2 h / 20 °C View Scheme |