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68733-20-0

Basic Information
CAS No.: 68733-20-0
Name: 1,3,4,6-TETRA-O-ACETYL-2-AZIDO-2-DEOXY-ALPHA-D-MANNOPYRANOSE
Article Data: 14
Molecular Structure:
Molecular Structure of 68733-20-0 (1,3,4,6-TETRA-O-ACETYL-2-AZIDO-2-DEOXY-ALPHA-D-MANNOPYRANOSE)
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
Synthetic route
108-24-7

acetic anhydride

115945-97-6

methyl 3-O-acetyl-2-azido-4,6-O-benzylidene-2-deoxy-α-D-mannopyranoside

68733-20-0

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-D-mannopyranoside

Conditions
ConditionsYield
With sulfuric acid at 0℃; for 1h;92%
108-24-7

acetic anhydride

(4aR,6S,7S,8R,8aS)-7-azido-6-methoxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-ol

68733-20-0

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-D-mannopyranoside

Conditions
ConditionsYield
With sulfuric acid at 20℃; for 2h;82%
108-24-7

acetic anhydride

116003-78-2

Methyl 2-azido-2-deoxy-4,6-O-(phenylmethylene)-α-D-mannopyranoside

68733-20-0

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-D-mannopyranoside

Conditions
ConditionsYield
With sulfuric acid at 20℃; for 2.5h;78%
With sulfuric acid at 20℃; for 0.666667h;75%
1600-27-7

mercury(II) diacetate

2873-29-2

D-glucal triacetate

A

56883-33-1

2-azido-2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranosyl acetate

B

80321-89-7

1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-β-D-glucopyranose

C

Acetic acid (2R,3R,4S,5R,6S)-4-acetoxy-2-acetoxymethyl-6-azido-5-chloro-tetrahydro-pyran-3-yl ester

D

68733-20-0

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-D-mannopyranoside

Conditions
ConditionsYield
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%
113544-40-4

1,3,4,6-tetra-O-acetyl-2-O-trifluoromethanesulfonyl-α-D-glucopyranose

68733-20-0

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-D-mannopyranoside

Conditions
ConditionsYield
With sodium azide In N,N-dimethyl-formamide at 60℃; for 0.5h;58%
With sodium azide In N,N-dimethyl-formamide20%
With sodium azide In N,N-dimethyl-formamide at 60℃; for 5h;10%
127-09-3

sodium acetate

668481-16-1

Acetic acid (2R,3S,4R)-4-acetoxy-2-acetoxymethyl-5-azido-6-nitrooxy-tetrahydro-pyran-3-yl ester

A

56883-33-1

2-azido-2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranosyl acetate

B

80321-89-7

1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-β-D-glucopyranose

C

68733-20-0

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-D-mannopyranoside

Conditions
ConditionsYield
In acetic acid at 100℃; for 1h;A n/a
B n/a
C 17%
127-09-3

sodium acetate

2873-29-2

D-glucal triacetate

A

56883-33-1

2-azido-2-deoxy-3,4,6-tri-O-acetyl-α-D-glucopyranosyl acetate

B

68733-20-0

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-D-mannopyranoside

Conditions
ConditionsYield
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;
127-09-3

sodium acetate

2873-29-2

D-glucal triacetate

68733-20-0

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-D-mannopyranoside

Conditions
ConditionsYield
With sodium azide; ammonium cerium(IV) nitrate 1.) acetonitrile, ethylacetate, -40 deg C; Yield given. Multistep reaction;
4692-12-0

1,3,4,6-tetra-O-acetyl glucopyranose

68733-20-0

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-D-mannopyranoside

Conditions
ConditionsYield
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
3162-96-7

methyl 4,6-O-benzylidene-α-D-glucopyranoside

68733-20-0

1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-D-mannopyranoside

Conditions
ConditionsYield
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
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