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

Base Information

• Chemical Name: (1S,3S,6S,7S,8S,9S)-6-(4-methoxybenzyl)-3-(N-methylamino)-5-azatricyclo[6.3.1.0^1,5]dodecane-7,9-diol
• CAS No.: 333999-61-4
• Molecular Formula: C₂₀H₃₀N₂O₃
• Molecular Weight: 346.47

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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

There total 28 articles about (1S,3S,6S,7S,8S,9S)-6-(4-methoxybenzyl)-3-(N-methylamino)-5-azatricyclo[6.3.1.0^1,5]dodecane-7,9-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:

(S)-2-[N-(4-methylphenyl)sulfonylamino]-3-(4-hydroxyphenyl) propionic acid (4703-32-6) → (1S,3S,6S,7S,8S,9S)-6-(4-methoxybenzyl)-3-(N-methylamino)-5-azatricyclo[6.3.1.01,5]dodecane-7,9-diol (333999-61-4)

Guidance literature:

Multi-step reaction with 13 steps

1: 73 percent / triphenylphosphine; NEt₃; pyridine / CCl₄; acetonitrile / 24 h / 27 - 30 °C

2: iodobenzene diacetate; 2,2,2-trifluoroethanol / 0.5 h / 20 °C

3: 0.48 g / pyridine; DMAP / 20 °C

4: 96 percent / H₂; PtO₂ / ethyl acetate / 20 °C / 760.05 Torr

5: 79 percent / K₂CO₃ / methanol

6: 97 percent / K₂CO₃ / acetone; dimethylformamide

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

8: 44 percent / sodium methoxide; water / methanol / 0.5 h / 20 °C

9: 93 percent / pyridine; DMAP / CH₂Cl₂ / 3 h / 20 °C

10: 95 percent / L-Selectride / tetrahydrofuran / 5 h / -78 °C

11: 72 percent / triethylamine; DMAP / CH₂Cl₂ / 2 h / -20 - 0 °C

12: 73 percent / 18-crown-6 / benzene / 2 h / 80 °C

13: LAH / tetrahydrofuran / 5 h / Heating

With pyridine; dmap; platinum(IV) oxide; lithium aluminium tetrahydride; tetrapropylammonium perruthennate; 18-crown-6 ether; 2,2,2-trifluoroethanol; [bis(acetoxy)iodo]benzene; 4 A molecular sieve; water; hydrogen; sodium methylate; L-Selectride; potassium carbonate; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile; benzene;

DOI:10.1021/ja016030z

Reference yield:

Ethyl N-(p-tosyl)tyrosinate (58559-09-4) → (1S,3S,6S,7S,8S,9S)-6-(4-methoxybenzyl)-3-(N-methylamino)-5-azatricyclo[6.3.1.01,5]dodecane-7,9-diol (333999-61-4)

Guidance literature:

Multi-step reaction with 14 steps

1: 98 percent / aq. NaOH / 0.5 h / Heating

2: 73 percent / triphenylphosphine; NEt₃; pyridine / CCl₄; acetonitrile / 24 h / 27 - 30 °C

3: iodobenzene diacetate; 2,2,2-trifluoroethanol / 0.5 h / 20 °C

4: 0.48 g / pyridine; DMAP / 20 °C

5: 96 percent / H₂; PtO₂ / ethyl acetate / 20 °C / 760.05 Torr

6: 79 percent / K₂CO₃ / methanol

7: 97 percent / K₂CO₃ / acetone; dimethylformamide

8: 77 percent / tetrapropylammonium perruthenate; 4-methylmorpholine N-oxide; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.25 h / 20 °C

9: 44 percent / sodium methoxide; water / methanol / 0.5 h / 20 °C

10: 93 percent / pyridine; DMAP / CH₂Cl₂ / 3 h / 20 °C

11: 95 percent / L-Selectride / tetrahydrofuran / 5 h / -78 °C

12: 72 percent / triethylamine; DMAP / CH₂Cl₂ / 2 h / -20 - 0 °C

13: 73 percent / 18-crown-6 / benzene / 2 h / 80 °C

14: LAH / tetrahydrofuran / 5 h / Heating

With pyridine; dmap; platinum(IV) oxide; sodium hydroxide; lithium aluminium tetrahydride; tetrapropylammonium perruthennate; 18-crown-6 ether; 2,2,2-trifluoroethanol; [bis(acetoxy)iodo]benzene; 4 A molecular sieve; water; hydrogen; sodium methylate; L-Selectride; potassium carbonate; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile; benzene;

DOI:10.1021/ja016030z

Reference yield:

L-tyrosine (60-18-4,18875-48-4,25619-78-7,30704-25-7) → (1S,3S,6S,7S,8S,9S)-6-(4-methoxybenzyl)-3-(N-methylamino)-5-azatricyclo[6.3.1.01,5]dodecane-7,9-diol (333999-61-4)

Guidance literature:

Multi-step reaction with 16 steps

1: 100 percent / HCl / 8 h / Heating

2: 98 percent / aq. Na₂CO₃ / CHCl₃ / 6 h / 20 °C

3: 98 percent / aq. NaOH / 0.5 h / Heating

4: 73 percent / triphenylphosphine; NEt₃; pyridine / CCl₄; acetonitrile / 24 h / 27 - 30 °C

5: iodobenzene diacetate; 2,2,2-trifluoroethanol / 0.5 h / 20 °C

6: 0.48 g / pyridine; DMAP / 20 °C

7: 96 percent / H₂; PtO₂ / ethyl acetate / 20 °C / 760.05 Torr

8: 79 percent / K₂CO₃ / methanol

9: 97 percent / K₂CO₃ / acetone; dimethylformamide

10: 77 percent / tetrapropylammonium perruthenate; 4-methylmorpholine N-oxide; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.25 h / 20 °C

11: 44 percent / sodium methoxide; water / methanol / 0.5 h / 20 °C

12: 93 percent / pyridine; DMAP / CH₂Cl₂ / 3 h / 20 °C

13: 95 percent / L-Selectride / tetrahydrofuran / 5 h / -78 °C

14: 72 percent / triethylamine; DMAP / CH₂Cl₂ / 2 h / -20 - 0 °C

15: 73 percent / 18-crown-6 / benzene / 2 h / 80 °C

16: LAH / tetrahydrofuran / 5 h / Heating

With pyridine; hydrogenchloride; dmap; platinum(IV) oxide; sodium hydroxide; lithium aluminium tetrahydride; tetrapropylammonium perruthennate; 18-crown-6 ether; 2,2,2-trifluoroethanol; [bis(acetoxy)iodo]benzene; 4 A molecular sieve; water; hydrogen; sodium methylate; L-Selectride; sodium carbonate; potassium carbonate; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; chloroform; ethyl acetate; N,N-dimethyl-formamide; acetone; acetonitrile; benzene;

DOI:10.1021/ja016030z

upstream raw materials:

(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

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

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

Ethyl N-(p-tosyl)tyrosinate

Downstream raw materials:

(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

(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

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