(2S,3R)-1-O-[(2'-azidoethyl)(hydroxy)phosphoryl]-2-(N-(tert-butoxycarbonyl)amino)-3-O-methoxymethyl-15-(4'-benzoylphenyl)-(4E)-pentadecene-1,3-diol

Base Information

• Chemical Name: (2S,3R)-1-O-[(2'-azidoethyl)(hydroxy)phosphoryl]-2-(N-(tert-butoxycarbonyl)amino)-3-O-methoxymethyl-15-(4'-benzoylphenyl)-(4E)-pentadecene-1,3-diol
• CAS No.: 855526-99-7
• Molecular Formula: C₃₇H₅₅N₄O₉P
• Molecular Weight: 730.839
• Mol file: 855526-99-7.mol

Synonyms:(2S,3R)-1-O-[(2'-azidoethyl)(hydroxy)phosphoryl]-2-(N-(tert-butoxycarbonyl)amino)-3-O-methoxymethyl-15-(4'-benzoylphenyl)-(4E)-pentadecene-1,3-diol

Chemical Property of (2S,3R)-1-O-[(2'-azidoethyl)(hydroxy)phosphoryl]-2-(N-(tert-butoxycarbonyl)amino)-3-O-methoxymethyl-15-(4'-benzoylphenyl)-(4E)-pentadecene-1,3-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-1-O-[(2'-azidoethyl)(hydroxy)phosphoryl]-2-(N-(tert-butoxycarbonyl)amino)-3-O-methoxymethyl-15-(4'-benzoylphenyl)-(4E)-pentadecene-1,3-diol

There total 10 articles about (2S,3R)-1-O-[(2'-azidoethyl)(hydroxy)phosphoryl]-2-(N-(tert-butoxycarbonyl)amino)-3-O-methoxymethyl-15-(4'-benzoylphenyl)-(4E)-pentadecene-1,3-diol 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:

[(E)-(1S,2R)-1-[(2-Azido-ethoxy)-chloro-phosphoryloxymethyl]-14-(4-benzoyl-phenyl)-2-methoxymethoxy-tetradec-3-enyl]-carbamic acid tert-butyl ester → (2S,3R)-1-O-[(2'-azidoethyl)(hydroxy)phosphoryl]-2-(N-(tert-butoxycarbonyl)amino)-3-O-methoxymethyl-15-(4'-benzoylphenyl)-(4E)-pentadecene-1,3-diol (855526-99-7)

Guidance literature:

With water; In diethyl ether; at 20 ℃;

DOI:10.1021/jo050513u

Reference yield:

dodec-11-en-1-ynyl-trimethyl-silane → (2S,3R)-1-O-[(2'-azidoethyl)(hydroxy)phosphoryl]-2-(N-(tert-butoxycarbonyl)amino)-3-O-methoxymethyl-15-(4'-benzoylphenyl)-(4E)-pentadecene-1,3-diol (855526-99-7)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 0.67 g / NaOH / diethyl ether; H₂O / 1 h / 20 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 2 h / -78 °C

2.2: 76 percent / HMPA / tetrahydrofuran; hexane / 2.5 h / -78 °C

3.1: 58 percent / Red-Al / diethyl ether; toluene / 4.17 h / 0 - 20 °C

4.1: 92 percent / iPr₂NEt / CH₂Cl₂ / 0 - 20 °C

5.1: 9-BBN-H / tetrahydrofuran / 20 °C

5.2: 73 percent / Pd(PPh₃)4; K₃PO₄ / tetrahydrofuran; dioxane; H₂O / 85 °C

6.1: 88 percent / acetic acid / H₂O / 5 h / 80 °C

7.1: pyridine / diethyl ether / Heating

8.1: 206 mg / H₂O / diethyl ether / 20 °C

With pyridine; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; water; acetic acid; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; toluene; 5.2: Suzuki coupling;

DOI:10.1021/jo050513u

Reference yield:

(S)-4-((E)-(R)-1-Hydroxy-trideca-2,12-dienyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (855526-95-3) → (2S,3R)-1-O-[(2'-azidoethyl)(hydroxy)phosphoryl]-2-(N-(tert-butoxycarbonyl)amino)-3-O-methoxymethyl-15-(4'-benzoylphenyl)-(4E)-pentadecene-1,3-diol (855526-99-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 92 percent / iPr₂NEt / CH₂Cl₂ / 0 - 20 °C

2.1: 9-BBN-H / tetrahydrofuran / 20 °C

2.2: 73 percent / Pd(PPh₃)4; K₃PO₄ / tetrahydrofuran; dioxane; H₂O / 85 °C

3.1: 88 percent / acetic acid / H₂O / 5 h / 80 °C

4.1: pyridine / diethyl ether / Heating

5.1: 206 mg / H₂O / diethyl ether / 20 °C

With pyridine; 9-borabicyclo[3.3.1]nonane dimer; water; acetic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; water; 2.2: Suzuki coupling;

DOI:10.1021/jo050513u

upstream raw materials:

(S)-4-((E)-(R)-1-Hydroxy-trideca-2,12-dienyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

(S)-4-((R)-1-Hydroxy-tridec-12-en-2-ynyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

(S)-4-((E)-(R)-1-Methoxymethoxy-trideca-2,12-dienyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

(2S,3R)-2-(N-(tert-butoxycarbonyl)amino)-3-O-methoxymethyl-15-(4'-benzoylphenyl)-(4E)-pentadecene-1,3-diol

Downstream raw materials:

(2S,3R)-1-O-[(2'-aminoethyl)(hydroxy)phosphoryl]-2-(N-(tert-butoxycarbonyl)amino)-3-O-methoxymethyl-15-(4'-benzoylphenyl)-(4E)-pentadecene-1,3-diol