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

Base Information

• Chemical Name: 1-(6-azidohexyl)-(3R,4R,5S)-4-acetylamino-5-N-tert-butoxycarbonylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate
• CAS No.: 1356826-62-4
• Molecular Formula: C₂₄H₄₄N₅O₇P
• Molecular Weight: 545.616
• Mol file: 1356826-62-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 16 articles about 1-(6-azidohexyl)-(3R,4R,5S)-4-acetylamino-5-N-tert-butoxycarbonylamino-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: 58.0%

methyl (6-azidohex-1-yl) [(3R,4R,5S)-4-acetamido-5-(1,1-dimethylethyloxycarbonylamino)-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate] (1332499-11-2) → 1-(6-azidohexyl)-(3R,4R,5S)-4-acetylamino-5-N-tert-butoxycarbonylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate (1356826-62-4)

Guidance literature:

With sodium iodide; In acetone; for 24h; Reflux; Inert atmosphere;

DOI:10.1039/c1ob05384a

Reference yield: 56.0%

methyl (3R,4R,5S)-4-acetamido-5-[(tert-butoxycarbonyl)-amino]-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate + 1-azido-6-bromohexane (235095-05-3) → 1-(6-azidohexyl)-(3R,4R,5S)-4-acetylamino-5-N-tert-butoxycarbonylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate (1356826-62-4)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; sodium iodide; In N,N-dimethyl-formamide; at 60 ℃;

DOI:10.1042/BCJ20180764

Reference yield:

C6H15N*C19H35N2O7P → 1-(6-azidohexyl)-(3R,4R,5S)-4-acetylamino-5-N-tert-butoxycarbonylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-phosphonate (1356826-62-4)

Guidance literature:

Multi-step reaction with 2 steps

1: acetonitrile / 1 h / Inert atmosphere

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

With sodium iodide; In 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]

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:

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