2-Azido-4,6-O-(R-benzylidene)-1,2,5-trideoxy-1,5-imino-N-methoxycarbonyl-3-O-methanesulfonyl-D-allitol

Base Information

Chemical Name:2-Azido-4,6-O-(R-benzylidene)-1,2,5-trideoxy-1,5-imino-N-methoxycarbonyl-3-O-methanesulfonyl-D-allitol
CAS No.:150271-35-5
Molecular Formula:C₁₆H₂₀N₄O₇S
Molecular Weight:412.423
Hs Code.:

Synonyms:2-Azido-4,6-O-(R-benzylidene)-1,2,5-trideoxy-1,5-imino-N-methoxycarbonyl-3-O-methanesulfonyl-D-allitol

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Chemical Property of 2-Azido-4,6-O-(R-benzylidene)-1,2,5-trideoxy-1,5-imino-N-methoxycarbonyl-3-O-methanesulfonyl-D-allitol

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Technology Process of 2-Azido-4,6-O-(R-benzylidene)-1,2,5-trideoxy-1,5-imino-N-methoxycarbonyl-3-O-methanesulfonyl-D-allitol

There total 9 articles about 2-Azido-4,6-O-(R-benzylidene)-1,2,5-trideoxy-1,5-imino-N-methoxycarbonyl-3-O-methanesulfonyl-D-allitol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 92.0%

: 124-63-0
methanesulfonyl chloride

: 150271-34-4
2-Azido-4,6-O-(R-benzylidene)-1,2,5-trideoxy-1,5-imino-N-methoxycarbonyl-D-allitol

: 150271-35-5
2-Azido-4,6-O-(R-benzylidene)-1,2,5-trideoxy-1,5-imino-N-methoxycarbonyl-3-O-methanesulfonyl-D-allitol

Guidance literature:: With pyridine; at 22 ℃; for 30h;

Reference yield:

: 130539-12-7
N-Benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-glucitol

: 150271-35-5
2-Azido-4,6-O-(R-benzylidene)-1,2,5-trideoxy-1,5-imino-N-methoxycarbonyl-3-O-methanesulfonyl-D-allitol

Guidance literature:: Multi-step reaction with 8 steps

1: 54 percent / p-toluenesulfonic acid / dimethylformamide / 4 h / 60 - 65 °C

2: 1.) di-n-butyltin oxide, 2.) triethylamine / 1.) MeOH, reflux, 2 h, 2.) CH₂Cl₂, 0 deg C, 30 min; 20 deg C, 3 h

3: 75 percent / NaH / tetrahydrofuran / 18 h / 25 °C

4: 44 percent / NaN₃, NH₄Cl / 2-methoxy-ethanol / 36 h / Heating

5: 95 percent / pyridine / 20 h / 22 °C

6: 52 percent / 18-crown-6 / toluene / 72 h / Heating

7: 35 percent / methanol / 18 h / Heating

8: 92 percent / pyridine / 30 h / 22 °C

With pyridine; sodium azide; 18-crown-6 ether; sodium hydride; di(n-butyl)tin oxide; ammonium chloride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; 2-methoxy-ethanol; N,N-dimethyl-formamide; toluene;

Reference yield:

: 19130-96-2
1,5-dideoxy-1,5-imino-D-glucitol

: 150271-35-5
2-Azido-4,6-O-(R-benzylidene)-1,2,5-trideoxy-1,5-imino-N-methoxycarbonyl-3-O-methanesulfonyl-D-allitol

Guidance literature:: Multi-step reaction with 9 steps

1: 54 percent / aq. NaHCO₃ / 18 h / Ambient temperature

2: 54 percent / p-toluenesulfonic acid / dimethylformamide / 4 h / 60 - 65 °C

3: 1.) di-n-butyltin oxide, 2.) triethylamine / 1.) MeOH, reflux, 2 h, 2.) CH₂Cl₂, 0 deg C, 30 min; 20 deg C, 3 h

4: 75 percent / NaH / tetrahydrofuran / 18 h / 25 °C

5: 44 percent / NaN₃, NH₄Cl / 2-methoxy-ethanol / 36 h / Heating

6: 95 percent / pyridine / 20 h / 22 °C

7: 52 percent / 18-crown-6 / toluene / 72 h / Heating

8: 35 percent / methanol / 18 h / Heating

9: 92 percent / pyridine / 30 h / 22 °C

With pyridine; sodium azide; 18-crown-6 ether; sodium hydride; di(n-butyl)tin oxide; sodium hydrogencarbonate; ammonium chloride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; 2-methoxy-ethanol; N,N-dimethyl-formamide; toluene;