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55287-49-5

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Basic Information
CAS No.: 55287-49-5
Name: BENZYL 2-ACETAMIDO-3,6-DI-O-BENZYL-2-DEOXY-ALPHA-D-GLUCOPYRANOSIDE
Article Data: 14
Molecular Structure:
Molecular Structure of 55287-49-5 (BENZYL 2-ACETAMIDO-3,6-DI-O-BENZYL-2-DEOXY-ALPHA-D-GLUCOPYRANOSIDE)
Formula: C29H33 N O6
Molecular Weight: 491.584
Synonyms: BENZYL 2-ACETAMIDO-3,6-DI-O-BENZYL-2-DEOXY-ALPHA-D-GLUCOPYRANOSIDE;2-Acetamido-1,3,6-tri-O-benzyl-2-deoxy-a-D-glucopyranoside
Density: 1.234g/cm3
Melting Point: 140-141°C
Boiling Point: 694.641°C at 760 mmHg
Flash Point: 373.905°C
PSA: 86.25000
LogP: 3.98680
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benzyl 2-acetamido-3-O-benzyl-2-deoxy-6-O-tosyl-α-D-glucopyranoside

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sodium phenyl-methanolate

55287-49-5

benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

Conditions
ConditionsYield
In N,N-dimethyl-formamide; benzyl alcohol at 90℃; for 1h;88%
14146-27-1

benzyl 3-O-benzyl-2-acetamido-2-deoxy-α-D-glucopyranoside

100-39-0

benzyl bromide

55287-49-5

benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

Conditions
ConditionsYield
With calcium sulfate; silver(l) oxide In chloroform for 16h;86%
With tetrabutylammomium bromide; bis(tri-n-butyltin)oxide 1.) toluene, reflux, 4 h, 2.) 80 deg C, 48 h; Yield given. Multistep reaction;

C29H31NO6

55287-49-5

benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

Conditions
ConditionsYield
With triethylsilane; boron trifluoride diethyl etherate In dichloromethane at 0℃; for 2h;72%
14146-26-0

benzyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside

55287-49-5

benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

Conditions
ConditionsYield
With hydrogenchloride; 3 A molecular sieve; sodium cyanoborohydride In tetrahydrofuran; diethyl ether at 0℃; for 0.166667h;60%
With hydrogenchloride; 3 A molecular sieve; sodium cyanoborohydride In tetrahydrofuran for 0.75h; Yield given;
14146-27-1

benzyl 3-O-benzyl-2-acetamido-2-deoxy-α-D-glucopyranoside

100-44-7

benzyl chloride

A

55287-54-2

3,4-di-O-benzyl-2-acetamido-2-desoxy-α-benzyl-D-glucopyranoside

B

55287-49-5

benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

C

38416-56-7

3,4,6-tri-O-benzyl-2-acetamido-2-desoxy-α-benzyl-D-glucopyranoside

Conditions
ConditionsYield
With sodium isopropylate In N,N-dimethyl-formamide at 20℃; for 15h;A 15%
B 50%
C 5%
...Expand
14146-27-1

benzyl 3-O-benzyl-2-acetamido-2-deoxy-α-D-glucopyranoside

100-39-0

benzyl bromide

A

55287-54-2

3,4-di-O-benzyl-2-acetamido-2-desoxy-α-benzyl-D-glucopyranoside

B

55287-49-5

benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

C

38416-56-7

3,4,6-tri-O-benzyl-2-acetamido-2-desoxy-α-benzyl-D-glucopyranoside

Conditions
ConditionsYield
With barium hydroxide octahydrate; barium(II) oxide In N,N-dimethyl-formamide at -5℃; for 4h;A 8.2%
B 39%
C 25%
With potassium hydroxide In N,N-dimethyl-formamide at 70 - 90℃;A 18%
B 21%
C 25%
...Expand

(2,2,2-Trichloro-acetyl)-carbamic acid (2R,3S,4R,5R,6S)-5-acetylamino-4,6-bis-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yl ester

55287-49-5

benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

Conditions
ConditionsYield
Stage #1: (2,2,2-Trichloro-acetyl)-carbamic acid (2R,3S,4R,5R,6S)-5-acetylamino-4,6-bis-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yl ester With polystyrene-bound [1,3,2]diazaphosphinane In dichloromethane at 20℃; for 0.166667h;
Stage #2: With potassium hydroxide In methanol at 60℃; for 3h;
1125-88-8

benzaldehyde dimethyl acetal

55287-49-5

benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 62 percent / p-toluenesulphonic acid / acetonitrile / 60 h / 60 °C
2: 1.) NaH / 1.) THF, 2.) THF
3: NaCNBH3, molecular sieves 3 Angstroem, etheral HCl / tetrahydrofuran / 0.75 h
View Scheme
100-39-0

benzyl bromide

alcoholic potash

alcoholic potash

55287-49-5

benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) NaH / 1.) THF, 2.) THF
2: NaCNBH3, molecular sieves 3 Angstroem, etheral HCl / tetrahydrofuran / 0.75 h
View Scheme
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benzyl 4,6-O-benzylidene-2-acetylamino-2-deoxy-α-D-glucopyranoside

55287-49-5

benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1.) NaH / 1.) THF, 2.) THF
2: NaCNBH3, molecular sieves 3 Angstroem, etheral HCl / tetrahydrofuran / 0.75 h
View Scheme
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