(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

Base Information

• Chemical Name: (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
• CAS No.: 333999-62-5
• Molecular Formula: C₂₈H₃₆N₂O₅
• Molecular Weight: 480.604
• Mol file: 333999-62-5.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 54 articles about (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 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:

benzyl chloroformate (501-53-1,94274-21-2) + (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) → (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)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃;

DOI:10.1021/ja016030z

Reference yield:

(S)-2-[N-(4-methylphenyl)sulfonylamino]-3-(4-hydroxyphenyl) propionic acid (4703-32-6) → (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)

Guidance literature:

Multi-step reaction with 14 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

14: 0.035 g / NEt₃ / CH₂Cl₂ / 20 °C

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)-3-(N-benzyloxycarbonyl-N-methylamino)-6-(4-methoxybenzyl)-5-azatricyclo[6.3.1.01,5]dodecane-7,9-diol (333999-62-5)

Guidance literature:

Multi-step reaction with 15 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

15: 0.035 g / NEt₃ / CH₂Cl₂ / 20 °C

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

upstream raw materials:

benzyl chloroformate

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

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

Ethyl N-(p-tosyl)tyrosinate

Downstream raw materials:

(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