methyl (6-azidohex-1-yl) [(3R,4R,5S)-4-acetamido-5-(1,1-dimethylethyloxycarbonylamino)-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate]

Base Information

• Chemical Name: methyl (6-azidohex-1-yl) [(3R,4R,5S)-4-acetamido-5-(1,1-dimethylethyloxycarbonylamino)-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate]
• CAS No.: 1332499-11-2
• Molecular Formula: C₂₅H₄₆N₅O₇P
• Molecular Weight: 559.643
• Mol file: 1332499-11-2.mol

Synonyms:methyl (6-azidohex-1-yl) [(3R,4R,5S)-4-acetamido-5-(1,1-dimethylethyloxycarbonylamino)-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate]

Chemical Property of methyl (6-azidohex-1-yl) [(3R,4R,5S)-4-acetamido-5-(1,1-dimethylethyloxycarbonylamino)-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate]

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (6-azidohex-1-yl) [(3R,4R,5S)-4-acetamido-5-(1,1-dimethylethyloxycarbonylamino)-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate]

There total 7 articles about methyl (6-azidohex-1-yl) [(3R,4R,5S)-4-acetamido-5-(1,1-dimethylethyloxycarbonylamino)-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate] 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:

ammonium [methyl (3R,4R,5S)-4-acetamido-5-(1,1-dimethylethyloxycarbonylamino)-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate] (1158845-35-2) → methyl (6-azidohex-1-yl) [(3R,4R,5S)-4-acetamido-5-(1,1-dimethylethyloxycarbonylamino)-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate] (1332499-11-2)

Guidance literature:

Multi-step reaction with 2 steps

1: Amberlite IR-120 / water

2: acetonitrile / 1 h / Inert atmosphere

With Amberlite IR-120; In water; acetonitrile;

DOI:10.1039/c1ob05384a

Reference yield:

6-azido-O-triisopropylsilylhexane-1-ol (1332499-10-1) → methyl (6-azidohex-1-yl) [(3R,4R,5S)-4-acetamido-5-(1,1-dimethylethyloxycarbonylamino)-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate] (1332499-11-2)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran

2: 2,6-dimethylpyridine / dichloromethane / 0.5 h / -40 °C / Inert atmosphere

3: acetonitrile / 1 h / Inert atmosphere

With 2,6-dimethylpyridine; tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1039/c1ob05384a

Reference yield:

O-p-toluenesulfonyl-O'-triisopropylsilylhexane-1,6-diol (1332499-09-8) → methyl (6-azidohex-1-yl) [(3R,4R,5S)-4-acetamido-5-(1,1-dimethylethyloxycarbonylamino)-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate] (1332499-11-2)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium azide / N,N-dimethyl-formamide / 4 h / 0 °C / Inert atmosphere

2: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran

3: 2,6-dimethylpyridine / dichloromethane / 0.5 h / -40 °C / Inert atmosphere

4: acetonitrile / 1 h / Inert atmosphere

With 2,6-dimethylpyridine; sodium azide; tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1039/c1ob05384a

upstream raw materials:

6-azido-O-trifluoromethanesulfonylhexan-1-ol

ammonium [methyl (3R,4R,5S)-4-acetamido-5-(1,1-dimethylethyloxycarbonylamino)-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate]

O-p-toluenesulfonyl-O'-triisopropylsilylhexane-1,6-diol

6-azido-O-triisopropylsilylhexane-1-ol

Downstream raw materials:

1-(6-azidohexyl)-(3R,4R,5S)-4-acetylamino-5-N-tert-butoxycarbonylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate

C₅₈H₉₄N₁₀O₁₄P₂

(6-azidohexyl) (3R,4R,5S)-4-acetylamino-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonic acid

1,4-bis[1-(hex-1'-yl [(3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonic acid])-1H-1,2,3-triazol-4-yl]-benzene