(5S,6R)-7,10-dibenzyloxy-8-methoxy-6,9-dimethyl-1-p-toluenesulfonyl-5-(N-p-toluenesulfonyl)carbamoyloxy-1,2,5,6-tetrahydro-1-benzazocine

Base Information

Chemical Name:(5S*,6R*)-7,10-dibenzyloxy-8-methoxy-6,9-dimethyl-1-p-toluenesulfonyl-5-(N-p-toluenesulfonyl)carbamoyloxy-1,2,5,6-tetrahydro-1-benzazocine
CAS No.:129077-32-3
Molecular Formula:C₄₃H₄₄N₂O₉S₂
Molecular Weight:796.962
Hs Code.:

Synonyms:(5S*,6R*)-7,10-dibenzyloxy-8-methoxy-6,9-dimethyl-1-p-toluenesulfonyl-5-(N-p-toluenesulfonyl)carbamoyloxy-1,2,5,6-tetrahydro-1-benzazocine

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Chemical Property of (5S*,6R*)-7,10-dibenzyloxy-8-methoxy-6,9-dimethyl-1-p-toluenesulfonyl-5-(N-p-toluenesulfonyl)carbamoyloxy-1,2,5,6-tetrahydro-1-benzazocine

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Technology Process of (5S*,6R*)-7,10-dibenzyloxy-8-methoxy-6,9-dimethyl-1-p-toluenesulfonyl-5-(N-p-toluenesulfonyl)carbamoyloxy-1,2,5,6-tetrahydro-1-benzazocine

There total 7 articles about (5S*,6R*)-7,10-dibenzyloxy-8-methoxy-6,9-dimethyl-1-p-toluenesulfonyl-5-(N-p-toluenesulfonyl)carbamoyloxy-1,2,5,6-tetrahydro-1-benzazocine 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: 99.0%

: 129056-05-9
(5S*,6R*)-7,10-dibenzyloxy-5-hydroxy-8-methoxy-6,9-dimethyl-1-p-toluenesulfonyl-1,2,5,6-tetrahydro-1-benzazocine

: 4083-64-1
Tosyl isocyanate

: 129077-32-3
(5S*,6R*)-7,10-dibenzyloxy-8-methoxy-6,9-dimethyl-1-p-toluenesulfonyl-5-(N-p-toluenesulfonyl)carbamoyloxy-1,2,5,6-tetrahydro-1-benzazocine

Guidance literature:: In tetrahydrofuran; for 0.0833333h; Ambient temperature;
DOI:10.1039/c39900000468

Reference yield:

: 116438-11-0
6,9-dimethyl-7,10-dioxo-5,5-(ethylenedioxy)-8-methoxy-1-(p-tolylsulfonyl)-1,2,3,4,5,6,7,10-octahydro-1-benzazocine

: 129077-32-3
(5S*,6R*)-7,10-dibenzyloxy-8-methoxy-6,9-dimethyl-1-p-toluenesulfonyl-5-(N-p-toluenesulfonyl)carbamoyloxy-1,2,5,6-tetrahydro-1-benzazocine

Guidance literature:: Multi-step reaction with 6 steps

1: Na₂S₂O₄, n-Bu₄NHSO₄ / CH₂Cl₂ / 0.5 h / Ambient temperature

2: K₂CO₃, 18-crown-6 / tetrahydrofuran / 19 h / Heating

3: 96 percent / 37percent aq. HCl / tetrahydrofuran / 4.5 h / Ambient temperature

4: 1.) PhSeCl, 10percent aq. HCl, 2.) NaIO₄ / 1.) EtOAc, RT, 21 h, 2.) THF, RT, 22 h

5: 100 percent / DIBAL / tetrahydrofuran / 0.5 h / -70 °C

6: 99 percent / tetrahydrofuran / 0.08 h / Ambient temperature

With hydrogenchloride; sodium periodate; sodium dithionite; Phenylselenyl chloride; 18-crown-6 ether; tetra(n-butyl)ammonium hydrogensulfate; diisobutylaluminium hydride; potassium carbonate; In tetrahydrofuran; dichloromethane;

Reference yield:

: 100-39-0
benzyl bromide

: 129077-32-3
(5S*,6R*)-7,10-dibenzyloxy-8-methoxy-6,9-dimethyl-1-p-toluenesulfonyl-5-(N-p-toluenesulfonyl)carbamoyloxy-1,2,5,6-tetrahydro-1-benzazocine

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) Na₂S₂O₄, 2.) K₂CO₃ / 1.) Buⁿ4NHSO₄, 2.) 18-crown-6 / 1.) H₂O, CH₂Cl₂, room temperature, 2.) THF, reflux, 19 h

2: conc. HCl / tetrahydrofuran / 4.5 h / 0 °C

3: 1.) PhSeCl, 10percent HCl, 2.) NaIO₄ / 1.) AcOEt, RT, 18 h, 2.) H₂O, THF, 16 h

4: di-isobutylaluminium hydride (DIBAL) / tetrahydrofuran / 0.5 h / -70 °C

5: 99 percent / tetrahydrofuran / 0.08 h / Ambient temperature

With hydrogenchloride; sodium periodate; sodium dithionite; Phenylselenyl chloride; diisobutylaluminum hydride; potassium carbonate; 18-crown-6 ether; tetra(n-butyl)ammonium hydrogensulfate; In tetrahydrofuran;
DOI:10.1039/c39900000468