(1S,3S)-ethyl 2-(2-(benzyl(tert-butoxycarbonyl)amino)-acetyl)-3-formyl-8-hydroxy-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylate

Base Information

Chemical Name:(1S,3S)-ethyl 2-(2-(benzyl(tert-butoxycarbonyl)amino)-acetyl)-3-formyl-8-hydroxy-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylate
CAS No.:1448530-96-8
Molecular Formula:C₃₁H₃₈N₂O₉
Molecular Weight:582.651
Hs Code.:

(1S,3S)-ethyl 2-(2-(benzyl(tert-butoxycarbonyl)amino)-acetyl)-3-formyl-8-hydroxy-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylate

Synonyms:(1S,3S)-ethyl 2-(2-(benzyl(tert-butoxycarbonyl)amino)-acetyl)-3-formyl-8-hydroxy-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylate

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Chemical Property of (1S,3S)-ethyl 2-(2-(benzyl(tert-butoxycarbonyl)amino)-acetyl)-3-formyl-8-hydroxy-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylate

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Technology Process of (1S,3S)-ethyl 2-(2-(benzyl(tert-butoxycarbonyl)amino)-acetyl)-3-formyl-8-hydroxy-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylate

There total 9 articles about (1S,3S)-ethyl 2-(2-(benzyl(tert-butoxycarbonyl)amino)-acetyl)-3-formyl-8-hydroxy-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylate 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:

: 1448530-95-7
(1S,3S)-ethyl 2-(2-(benzyl(tert-butoxycarbonyl)amino)acetyl)-8-hydroxy-3-(hydroxymethyl)-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylate

: 1448530-96-8
(1S,3S)-ethyl 2-(2-(benzyl(tert-butoxycarbonyl)amino)-acetyl)-3-formyl-8-hydroxy-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylate

Guidance literature:: (1S,3S)-ethyl 2-(2-(benzyl(tert-butoxycarbonyl)amino)acetyl)-8-hydroxy-3-(hydroxymethyl)-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylate; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 0.5h; Inert atmosphere;

With triethylamine; In dichloromethane; at -78 - 0 ℃; for 0.75h; Inert atmosphere;
DOI:10.1016/j.tet.2013.05.009

Reference yield:

: 1448530-86-6
(1R,3S)-ethyl 5-bromo-3-(((tert-butyldimethylsilyl)oxy)-methyl)-8-hydroxy-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylate

: 1448530-96-8
(1S,3S)-ethyl 2-(2-(benzyl(tert-butoxycarbonyl)amino)-acetyl)-3-formyl-8-hydroxy-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: potassium carbonate / acetone / Inert atmosphere

2.1: 20% palladium hydroxide-activated charcoal; hydrogen / methanol / 2585.81 Torr / Inert atmosphere

3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 60 h / Inert atmosphere

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran; methanol / Inert atmosphere

5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

5.2: 0.75 h / -78 - 0 °C / Inert atmosphere

With oxalyl dichloride; 20% palladium hydroxide-activated charcoal; tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; methanol; dichloromethane; acetone;
DOI:10.1016/j.tet.2013.05.009

Reference yield:

: 1177255-31-0
bromotyrosinol

: 1448530-96-8
(1S,3S)-ethyl 2-(2-(benzyl(tert-butoxycarbonyl)amino)-acetyl)-3-formyl-8-hydroxy-7-methoxy-6-methyl-1,2,3,4-tetrahydroisoquinoline-1-carboxylate

Guidance literature:: Multi-step reaction with 9 steps

1.1: dmap; triethylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere

2.1: ammonium chloride / water; dichloromethane / 2 h / 20 °C / Inert atmosphere

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.42 h / 0 °C / Inert atmosphere

4.1: acetic acid / toluene; 2,2,2-trifluoroethanol; dichloromethane / Inert atmosphere; Molecular sieve

5.1: potassium carbonate / acetone / Inert atmosphere

6.1: 20% palladium hydroxide-activated charcoal; hydrogen / methanol / 2585.81 Torr / Inert atmosphere

7.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 60 h / Inert atmosphere

8.1: tetrabutyl ammonium fluoride / tetrahydrofuran; methanol / Inert atmosphere

9.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.5 h / -78 °C / Inert atmosphere

9.2: 0.75 h / -78 - 0 °C / Inert atmosphere

With dmap; oxalyl dichloride; 20% palladium hydroxide-activated charcoal; tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; ammonium chloride; acetic acid; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; 2,2,2-trifluoroethanol; water; acetone; toluene;
DOI:10.1016/j.tet.2013.05.009