[(R)-1-(2-benzyloxymethyl-benzoyl)-3-(3,4-di methoxyphenyl)-propyl]-carbamic acid benzyl ester

Base Information

• Chemical Name: [(R)-1-(2-benzyloxymethyl-benzoyl)-3-(3,4-di methoxyphenyl)-propyl]-carbamic acid benzyl ester
• CAS No.: 1456722-48-7
• Molecular Formula: C₃₄H₃₅NO₆
• Molecular Weight: 553.655

Synonyms:[(R)-1-(2-benzyloxymethyl-benzoyl)-3-(3,4-di methoxyphenyl)-propyl]-carbamic acid benzyl ester

Chemical Property of [(R)-1-(2-benzyloxymethyl-benzoyl)-3-(3,4-di methoxyphenyl)-propyl]-carbamic acid benzyl ester

Chemical Property:

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Technology Process of [(R)-1-(2-benzyloxymethyl-benzoyl)-3-(3,4-di methoxyphenyl)-propyl]-carbamic acid benzyl ester

There total 7 articles about [(R)-1-(2-benzyloxymethyl-benzoyl)-3-(3,4-di methoxyphenyl)-propyl]-carbamic acid benzyl ester 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: 74.0%

[(R)-3-(3,4-dimethoxy-phenyl)-1-(methoxymethyl-carbamoyl)-propyl]-carbamic acid benzyl ester (1456722-47-6) + 1-((benzyloxy)methyl)-2-bromobenzene (81395-28-0) → [(R)-1-(2-benzyloxymethyl-benzoyl)-3-(3,4-di methoxyphenyl)-propyl]-carbamic acid benzyl ester (1456722-48-7)

Guidance literature:

1-bromo-2-[(benzyloxy)methyl]benzene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.25h; Inert atmosphere;

[(R)-3-(3,4-dimethoxy-phenyl)-1-(methoxymethyl-carbamoyl)-propyl]-carbamic acid benzyl ester; In tetrahydrofuran; hexane; at -78 - -20 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.tet.2013.08.042

Reference yield:

(4S)-3-benzyloxycarbonyl-2,2-dimethyloxazolidine-4-carbaldehyde (117833-92-8) → [(R)-1-(2-benzyloxymethyl-benzoyl)-3-(3,4-di methoxyphenyl)-propyl]-carbamic acid benzyl ester (1456722-48-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: n-butyllithium / tetrahydrofuran / 0.58 h / -20 °C / Inert atmosphere

1.2: 1.75 h / -70 - -15 °C / Inert atmosphere

2.1: diphenyl sulfide; hydrogen; palladium 10% on activated carbon / methanol / 17 h / 20 °C / 760.05 Torr

3.1: toluene-4-sulfonic acid / methanol / 4 h / 20 °C / Inert atmosphere

4.1: [bis(acetoxy)iodo]benzene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / water; acetonitrile / 17 h / 0 - 20 °C / Inert atmosphere

5.1: 4-methyl-morpholine; isobutyl chloroformate / dichloromethane / 0.25 h / -15 °C / Inert atmosphere

5.2: 2 h / -15 - 20 °C / Inert atmosphere

6.1: n-butyllithium / hexane; tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere

6.2: 1 h / -78 - -20 °C / Inert atmosphere

With 4-methyl-morpholine; n-butyllithium; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; diphenyl sulfide; palladium 10% on activated carbon; hydrogen; toluene-4-sulfonic acid; isobutyl chloroformate; In tetrahydrofuran; methanol; hexane; dichloromethane; water; acetonitrile;

DOI:10.1016/j.tet.2013.08.042

Reference yield:

(R)-2-benzyloxycarbonylamino-4-(3,4-dimethoxy-phenyl)-butyric acid (1456722-46-5) → [(R)-1-(2-benzyloxymethyl-benzoyl)-3-(3,4-di methoxyphenyl)-propyl]-carbamic acid benzyl ester (1456722-48-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 4-methyl-morpholine; isobutyl chloroformate / dichloromethane / 0.25 h / -15 °C / Inert atmosphere

1.2: 2 h / -15 - 20 °C / Inert atmosphere

2.1: n-butyllithium / hexane; tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere

2.2: 1 h / -78 - -20 °C / Inert atmosphere

With 4-methyl-morpholine; n-butyllithium; isobutyl chloroformate; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1016/j.tet.2013.08.042

upstream raw materials:

(4S)-3-benzyloxycarbonyl-2,2-dimethyloxazolidine-4-carbaldehyde

(R)-2-benzyloxycarbonylamino-4-(3,4-dimethoxy-phenyl)-butyric acid

[(R)-3-(3,4-dimethoxy-phenyl)-1-(methoxymethyl-carbamoyl)-propyl]-carbamic acid benzyl ester

1-((benzyloxy)methyl)-2-bromobenzene

Downstream raw materials:

[(1S,2R)-1-(2-benzyloxymethyl-phenyl)-6,7-di-methoxy-1,2,3,4-tetrahydro-naphthalen-2-yl]-carbamic acid benzyl ester

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