(1S,3S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-2-((R)-1,2-diphenyl-ethyl)-8-hydroxy-5,7-dimethoxy-6-methyl-1,2,3,4-tetrahydro-isoquinoline-1-carboxylic acid ethyl ester

Base Information

Chemical Name:(1S,3S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-2-((R)-1,2-diphenyl-ethyl)-8-hydroxy-5,7-dimethoxy-6-methyl-1,2,3,4-tetrahydro-isoquinoline-1-carboxylic acid ethyl ester
CAS No.:866110-64-7
Molecular Formula:C₃₆H₄₉NO₆Si
Molecular Weight:619.874
Hs Code.:

(1S,3S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-2-((R)-1,2-diphenyl-ethyl)-8-hydroxy-5,7-dimethoxy-6-methyl-1,2,3,4-tetrahydro-isoquinoline-1-carboxylic acid ethyl ester

Synonyms:(1S,3S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-2-((R)-1,2-diphenyl-ethyl)-8-hydroxy-5,7-dimethoxy-6-methyl-1,2,3,4-tetrahydro-isoquinoline-1-carboxylic acid ethyl ester

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Chemical Property of (1S,3S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-2-((R)-1,2-diphenyl-ethyl)-8-hydroxy-5,7-dimethoxy-6-methyl-1,2,3,4-tetrahydro-isoquinoline-1-carboxylic acid ethyl ester

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Technology Process of (1S,3S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-2-((R)-1,2-diphenyl-ethyl)-8-hydroxy-5,7-dimethoxy-6-methyl-1,2,3,4-tetrahydro-isoquinoline-1-carboxylic acid ethyl ester

There total 7 articles about (1S,3S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-2-((R)-1,2-diphenyl-ethyl)-8-hydroxy-5,7-dimethoxy-6-methyl-1,2,3,4-tetrahydro-isoquinoline-1-carboxylic acid ethyl 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: 92.0%

: 866110-63-6
5-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-((R)-1,2-diphenyl-ethylamino)-propyl]-2,4-dimethoxy-3-methyl-phenol

: 924-44-7
glyoxylic acid ethyl ester

: 866110-64-7
(1S,3S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-2-((R)-1,2-diphenyl-ethyl)-8-hydroxy-5,7-dimethoxy-6-methyl-1,2,3,4-tetrahydro-isoquinoline-1-carboxylic acid ethyl ester

Guidance literature:: In toluene; acetonitrile; at 40 ℃; for 84h;
DOI:10.1021/ja0535918

Reference yield:

: (5-benzyloxy-2,4-dimethoxy-3-methyl-phenyl)-methanol

: 866110-64-7
(1S,3S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-2-((R)-1,2-diphenyl-ethyl)-8-hydroxy-5,7-dimethoxy-6-methyl-1,2,3,4-tetrahydro-isoquinoline-1-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: PPh₃; I₂; imidazole / CH₂Cl₂ / 0.5 h / 0 °C

2.1: NaHMDS / tetrahydrofuran / 0.75 h / -78 °C

2.2: 4.73 g / tetrahydrofuran / 4 h / -78 °C

3.1: H₂ / Pd/C / tetrahydrofuran; methanol / 18 h / 760 Torr

4.1: N-methylmorpholine; isobutyl chloroformate / tetrahydrofuran / 0.33 h / 20 °C

4.2: 740 mg / NaBH₄ / tetrahydrofuran; H₂O / 2 h / 0 °C

5.1: TFA / CH₂Cl₂ / 0.67 h / 20 °C

6.1: 4.15 g / NEt₃ / CH₂Cl₂ / 19 h / 20 °C

7.1: 92 percent / acetonitrile; toluene / 84 h / 40 °C

With 4-methyl-morpholine; 1H-imidazole; hydrogen; iodine; sodium hexamethyldisilazane; triethylamine; triphenylphosphine; trifluoroacetic acid; isobutyl chloroformate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; toluene; acetonitrile;
DOI:10.1021/ja0535918

Reference yield:

: 866110-56-7
1-Benzyloxy-5-iodomethyl-2,4-dimethoxy-3-methyl-benzene

: 866110-64-7
(1S,3S)-3-(tert-Butyl-dimethyl-silanyloxymethyl)-2-((R)-1,2-diphenyl-ethyl)-8-hydroxy-5,7-dimethoxy-6-methyl-1,2,3,4-tetrahydro-isoquinoline-1-carboxylic acid ethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: NaHMDS / tetrahydrofuran / 0.75 h / -78 °C

1.2: 4.73 g / tetrahydrofuran / 4 h / -78 °C

2.1: H₂ / Pd/C / tetrahydrofuran; methanol / 18 h / 760 Torr

3.1: N-methylmorpholine; isobutyl chloroformate / tetrahydrofuran / 0.33 h / 20 °C

3.2: 740 mg / NaBH₄ / tetrahydrofuran; H₂O / 2 h / 0 °C

4.1: TFA / CH₂Cl₂ / 0.67 h / 20 °C

5.1: 4.15 g / NEt₃ / CH₂Cl₂ / 19 h / 20 °C

6.1: 92 percent / acetonitrile; toluene / 84 h / 40 °C

With 4-methyl-morpholine; hydrogen; sodium hexamethyldisilazane; triethylamine; trifluoroacetic acid; isobutyl chloroformate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; toluene; acetonitrile;
DOI:10.1021/ja0535918