(2S,5S,6S,7R,8S,10aS)-2-[[(benzyloxy)carbonyl]methylamino]octahydro-6-hydroxy-5-[(4-methoxyphenyl)methyl]-1H-7,10a-methanopyrrolo[1,2-a]azocin-8-yl dibenzyl phosphate

Base Information

• Chemical Name: (2S,5S,6S,7R,8S,10aS)-2-[[(benzyloxy)carbonyl]methylamino]octahydro-6-hydroxy-5-[(4-methoxyphenyl)methyl]-1H-7,10a-methanopyrrolo[1,2-a]azocin-8-yl dibenzyl phosphate
• CAS No.: 248948-75-6
• Molecular Formula: C₄₂H₄₉N₂O₈P
• Molecular Weight: 740.833
• Mol file: 248948-75-6.mol

Synonyms:(2S,5S,6S,7R,8S,10aS)-2-[[(benzyloxy)carbonyl]methylamino]octahydro-6-hydroxy-5-[(4-methoxyphenyl)methyl]-1H-7,10a-methanopyrrolo[1,2-a]azocin-8-yl dibenzyl phosphate

Chemical Property of (2S,5S,6S,7R,8S,10aS)-2-[[(benzyloxy)carbonyl]methylamino]octahydro-6-hydroxy-5-[(4-methoxyphenyl)methyl]-1H-7,10a-methanopyrrolo[1,2-a]azocin-8-yl dibenzyl phosphate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5S,6S,7R,8S,10aS)-2-[[(benzyloxy)carbonyl]methylamino]octahydro-6-hydroxy-5-[(4-methoxyphenyl)methyl]-1H-7,10a-methanopyrrolo[1,2-a]azocin-8-yl dibenzyl phosphate

There total 106 articles about (2S,5S,6S,7R,8S,10aS)-2-[[(benzyloxy)carbonyl]methylamino]octahydro-6-hydroxy-5-[(4-methoxyphenyl)methyl]-1H-7,10a-methanopyrrolo[1,2-a]azocin-8-yl dibenzyl phosphate 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: 96.0%

(2S,5S,6S,7R,8S,10aS)-2-[[(benzyloxy)carbonyl]methylamino]-6-(triethylsilyloxy)octahydro-5-[(4-methoxyphenyl)methyl]-1H-7,10a-methanopyrrolo[1,2-a]azocin-8-yl dibenzyl phosphate (248948-72-3) → (2S,5S,6S,7R,8S,10aS)-2-[[(benzyloxy)carbonyl]methylamino]octahydro-6-hydroxy-5-[(4-methoxyphenyl)methyl]-1H-7,10a-methanopyrrolo[1,2-a]azocin-8-yl dibenzyl phosphate (248948-75-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃; for 2h;

DOI:10.1021/ja991160h

Reference yield: 61.0%

Dibenzyl N,N-diisopropylphosphoramidite (108549-23-1) + (1S,3S,6S,7S,8S,9S)-3-(N-benzyloxycarbonyl-N-methylamino)-6-(4-methoxybenzyl)-5-azatricyclo[6.3.1.01,5]dodecane-7,9-diol (333999-62-5) → (2S,5S,6S,7R,8S,10aS)-2-[[(benzyloxy)carbonyl]methylamino]octahydro-6-hydroxy-5-[(4-methoxyphenyl)methyl]-1H-7,10a-methanopyrrolo[1,2-a]azocin-8-yl dibenzyl phosphate (248948-75-6)

Guidance literature:

Dibenzyl N,N-diisopropylphosphoramidite; (1S,3S,6S,7S,8S,9S)-3-(N-benzyloxycarbonyl-N-methylamino)-6-(4-methoxybenzyl)-5-azatricyclo[6.3.1.0^1,5]dodecane-7,9-diol; With 1H-tetrazole; In dichloromethane; at 0 ℃; for 2.8h;

With triethylamine; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -78 ℃; for 0.5h;

DOI:10.1021/ol301331t

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → (2S,5S,6S,7R,8S,10aS)-2-[[(benzyloxy)carbonyl]methylamino]octahydro-6-hydroxy-5-[(4-methoxyphenyl)methyl]-1H-7,10a-methanopyrrolo[1,2-a]azocin-8-yl dibenzyl phosphate (248948-75-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 0.035 g / NEt₃ / CH₂Cl₂ / 20 °C

2.1: 1-H-tetrazole / CH₂Cl₂ / 1.5 h / 0 °C

2.2: 29 percent / t-BuOOH / decane; CH₂Cl₂ / 1 h / -78 °C

With 1H-tetrazole; triethylamine; In dichloromethane;

DOI:10.1021/ja016030z

upstream raw materials:

(2S,5S,6S,7R,8S,10aS)-2-[[(benzyloxy)carbonyl]methylamino]-6-(triethylsilyloxy)octahydro-5-[(4-methoxyphenyl)methyl]-1H-7,10a-methanopyrrolo[1,2-a]azocin-8-yl dibenzyl phosphate

Dibenzyl N,N-diisopropylphosphoramidite

(1S,3S,6S,7S,8S,9S)-3-(N-benzyloxycarbonyl-N-methylamino)-6-(4-methoxybenzyl)-5-azatricyclo[6.3.1.0^1,5]dodecane-7,9-diol

benzyl chloroformate