(1S,3S,6S,7S,8R)-7-hydroxy-6-(4-methoxybenzyl)-3-[N-methyl-N-(4-methylphenyl)sulfonylamino]-5-azatricyclo[6.3.1.0^1,5]dodecan-4,9-dione

Base Information

• Chemical Name: (1S,3S,6S,7S,8R)-7-hydroxy-6-(4-methoxybenzyl)-3-[N-methyl-N-(4-methylphenyl)sulfonylamino]-5-azatricyclo[6.3.1.0^1,5]dodecan-4,9-dione
• CAS No.: 333999-57-8
• Molecular Formula: C₂₇H₃₂N₂O₆S
• Molecular Weight: 512.627

Synonyms:(1S,3S,6S,7S,8R)-7-hydroxy-6-(4-methoxybenzyl)-3-[N-methyl-N-(4-methylphenyl)sulfonylamino]-5-azatricyclo[6.3.1.0^1,5]dodecan-4,9-dione

Chemical Property of (1S,3S,6S,7S,8R)-7-hydroxy-6-(4-methoxybenzyl)-3-[N-methyl-N-(4-methylphenyl)sulfonylamino]-5-azatricyclo[6.3.1.0^1,5]dodecan-4,9-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (1S,3S,6S,7S,8R)-7-hydroxy-6-(4-methoxybenzyl)-3-[N-methyl-N-(4-methylphenyl)sulfonylamino]-5-azatricyclo[6.3.1.0^1,5]dodecan-4,9-dione

There total 12 articles about (1S,3S,6S,7S,8R)-7-hydroxy-6-(4-methoxybenzyl)-3-[N-methyl-N-(4-methylphenyl)sulfonylamino]-5-azatricyclo[6.3.1.0^1,5]dodecan-4,9-dione 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: 44.0%

(3S,1S')-1-[1'-formyl-2'-(4-methoxyphenyl)-ethyl]-3-[N-methyl-N-(4-methylphenyl)sulfonylamino]-1-azaspiro[4.5]decan-2,8-dione (333999-56-7) → (1S,3S,6S,7S,8R)-7-hydroxy-6-(4-methoxybenzyl)-3-[N-methyl-N-(4-methylphenyl)sulfonylamino]-5-azatricyclo[6.3.1.01,5]dodecan-4,9-dione (333999-57-8)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 0.5h;

DOI:10.1016/j.tet.2006.01.111

Reference yield:

(S)-2-[N-(4-methylphenyl)sulfonylamino]-3-(4-hydroxyphenyl) propionic acid (4703-32-6) → (1S,3S,6S,7S,8R)-7-hydroxy-6-(4-methoxybenzyl)-3-[N-methyl-N-(4-methylphenyl)sulfonylamino]-5-azatricyclo[6.3.1.01,5]dodecan-4,9-dione (333999-57-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 73 percent / PPh₃; NEt₃; pyridine / acetonitrile; CCl₄ / 24 h / 30 °C

2: PhI(OAc)2 / 2,2,2-trifluoro-ethanol / 0.5 h / 25 °C

3: 41 percent / pyridine; 4-(dimethylamino)pyridine / 25 °C

4: 96 percent / H₂ / PtO₂ / ethyl acetate / 25 °C / 760 Torr

5: 79 percent / K₂CO₃ / methanol / 25 °C

6: 97 percent / K₂CO₃ / acetone; dimethylformamide / 12 h / 25 °C

7: 77 percent / 4-methylmorpholine-N-oxide; Pr₄NRuO₄; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.25 h / 20 °C

8: 44 percent / NaOMe / aq. methanol / 0.5 h / 20 °C

With pyridine; dmap; tetrapropylammonium perruthennate; [bis(acetoxy)iodo]benzene; 4 A molecular sieve; hydrogen; sodium methylate; potassium carbonate; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; platinum(IV) oxide; In methanol; tetrachloromethane; dichloromethane; 2,2,2-trifluoroethanol; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile; 7: Ley oxidation;

DOI:10.1016/j.tet.2006.01.111

Reference yield:

N-{(S)-1-[(S)-1-Hydroxymethyl-2-(4-methoxy-phenyl)-ethyl]-2,8-dioxo-1-aza-spiro[4.5]deca-6,9-dien-3-yl}-4-methyl-benzenesulfonamide (333999-51-2) → (1S,3S,6S,7S,8R)-7-hydroxy-6-(4-methoxybenzyl)-3-[N-methyl-N-(4-methylphenyl)sulfonylamino]-5-azatricyclo[6.3.1.01,5]dodecan-4,9-dione (333999-57-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 41 percent / pyridine; 4-(dimethylamino)pyridine / 25 °C

2: 96 percent / H₂ / PtO₂ / ethyl acetate / 25 °C / 760 Torr

3: 79 percent / K₂CO₃ / methanol / 25 °C

4: 97 percent / K₂CO₃ / acetone; dimethylformamide / 12 h / 25 °C

5: 77 percent / 4-methylmorpholine-N-oxide; Pr₄NRuO₄; molecular sieves 4 Angstroem / CH₂Cl₂ / 0.25 h / 20 °C

6: 44 percent / NaOMe / aq. methanol / 0.5 h / 20 °C

With pyridine; dmap; tetrapropylammonium perruthennate; 4 A molecular sieve; hydrogen; sodium methylate; potassium carbonate; 4-methylmorpholine N-oxide; platinum(IV) oxide; In methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; 5: Ley oxidation;

DOI:10.1016/j.tet.2006.01.111

upstream raw materials:

(3S,1S')-1-[1'-formyl-2'-(4-methoxyphenyl)-ethyl]-3-[N-methyl-N-(4-methylphenyl)sulfonylamino]-1-azaspiro[4.5]decan-2,8-dione

(S)-2-[N-(4-methylphenyl)sulfonylamino]-3-(4-hydroxyphenyl) propionic acid

N-{(S)-1-[(S)-1-Hydroxymethyl-2-(4-methoxy-phenyl)-ethyl]-2,8-dioxo-1-aza-spiro[4.5]deca-6,9-dien-3-yl}-4-methyl-benzenesulfonamide

(S)-2-{(S)-1-[N-(4-methylphenyl)sulfonylamino]-2-(4-hydroxyphenyl)ethyl}-4-(4-methoxybenzyl)-2-oxazoline

Downstream raw materials:

(1S,3S,6S,7S,8R)-7-acetoxy-6-(4-methoxybenzyl)-3-[N-methyl-N-(4-methylphenyl)sulfonylamino]-5-azatricyclo[6.3.1.0^1,5]dodecan-4,9-dione

Phosphoric acid dibenzyl ester (1S,3S,6S,7S,8R,9S)-7-hydroxy-6-(4-methoxy-benzyl)-3-methylamino-5-aza-tricyclo[6.3.1.0^1,5]dodec-9-yl ester

(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

(1S,3S,6S,7S,8R,9R)-7-acetoxy-6-(4-methoxybenzyl)-3-[N-methyl-N-(4-methylphenyl)sulfonylamino]-9-[(4-nitrophenyl)sulfonyloxy]-5-azatricyclo[6.3.1.0^1,5]dodecan-4-one

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