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

Base Information

• Chemical Name: (6-azidohexyl) (3R,4R,5S)-4-acetylamino-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonic acid
• CAS No.: 1332499-16-7
• Molecular Formula: C₁₉H₃₆N₅O₅P
• Molecular Weight: 445.499
• Mol file: 1332499-16-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 16 articles about (6-azidohexyl) (3R,4R,5S)-4-acetylamino-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonic acid 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: 91.0%

1-(6-azidohexyl)-(3R,4R,5S)-4-acetylamino-5-N-tert-butoxycarbonylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate (1356826-62-4) → (6-azidohexyl) (3R,4R,5S)-4-acetylamino-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonic acid (1332499-16-7)

Guidance literature:

With trifluoroacetic acid; In 1,4-dioxane; water;

DOI:10.1039/c1ob05384a

Reference yield:

methyl (6-azidohex-1-yl) [(3R,4R,5S)-4-acetamido-5-(1,1-dimethylethyloxycarbonylamino)-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate] (1332499-11-2) → (6-azidohexyl) (3R,4R,5S)-4-acetylamino-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonic acid (1332499-16-7)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium iodide / acetone / 24 h / Reflux; Inert atmosphere

2: trifluoroacetic acid / 1,4-dioxane; water

With trifluoroacetic acid; sodium iodide; In 1,4-dioxane; water; acetone;

DOI:10.1039/c1ob05384a

Reference yield:

C6H15N*C19H35N2O7P → (6-azidohexyl) (3R,4R,5S)-4-acetylamino-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonic acid (1332499-16-7)

Guidance literature:

Multi-step reaction with 3 steps

1: acetonitrile / 1 h / Inert atmosphere

2: sodium iodide / acetone / 24 h / Reflux; Inert atmosphere

3: trifluoroacetic acid / 1,4-dioxane; water

With trifluoroacetic acid; sodium iodide; In 1,4-dioxane; water; acetone; acetonitrile;

DOI:10.1039/c1ob05384a

upstream raw materials:

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

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

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