(3S,5S,6R)-3-[5-(tert-Butyl-dimethyl-silanyloxy)-2,4-dimethoxy-3-methyl-benzyl]-4-methyl-5,6-diphenyl-morpholin-2-one

Base Information

Chemical Name:(3S,5S,6R)-3-[5-(tert-Butyl-dimethyl-silanyloxy)-2,4-dimethoxy-3-methyl-benzyl]-4-methyl-5,6-diphenyl-morpholin-2-one
CAS No.:866110-60-3
Molecular Formula:C₃₃H₄₃NO₅Si
Molecular Weight:561.794
Hs Code.:

Synonyms:(3S,5S,6R)-3-[5-(tert-Butyl-dimethyl-silanyloxy)-2,4-dimethoxy-3-methyl-benzyl]-4-methyl-5,6-diphenyl-morpholin-2-one

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Chemical Property of (3S,5S,6R)-3-[5-(tert-Butyl-dimethyl-silanyloxy)-2,4-dimethoxy-3-methyl-benzyl]-4-methyl-5,6-diphenyl-morpholin-2-one

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Technology Process of (3S,5S,6R)-3-[5-(tert-Butyl-dimethyl-silanyloxy)-2,4-dimethoxy-3-methyl-benzyl]-4-methyl-5,6-diphenyl-morpholin-2-one

There total 6 articles about (3S,5S,6R)-3-[5-(tert-Butyl-dimethyl-silanyloxy)-2,4-dimethoxy-3-methyl-benzyl]-4-methyl-5,6-diphenyl-morpholin-2-one 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: 72.0%

: 866110-59-0
(3S,5S,6R)-3-[5-(tert-Butyl-dimethyl-silanyloxy)-2,4-dimethoxy-3-methyl-benzyl]-5,6-diphenyl-morpholin-2-one

: 50-00-0,30525-89-4,61233-19-0
formaldehyd

: 866110-60-3
(3S,5S,6R)-3-[5-(tert-Butyl-dimethyl-silanyloxy)-2,4-dimethoxy-3-methyl-benzyl]-4-methyl-5,6-diphenyl-morpholin-2-one

Guidance literature:: (3S,5S,6R)-3-[5-(tert-Butyl-dimethyl-silanyloxy)-2,4-dimethoxy-3-methyl-benzyl]-5,6-diphenyl-morpholin-2-one; formaldehyd; In tetrahydrofuran; water; acetonitrile; at 20 ℃; for 0.25h;

With sodium cyanoborohydride; acetic acid; In tetrahydrofuran; acetonitrile; at 20 ℃; for 0.75h;
DOI:10.1021/ja0535918

Reference yield:

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

: 866110-60-3
(3S,5S,6R)-3-[5-(tert-Butyl-dimethyl-silanyloxy)-2,4-dimethoxy-3-methyl-benzyl]-4-methyl-5,6-diphenyl-morpholin-2-one

Guidance literature:: Multi-step reaction with 6 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/BaSO₄ / tetrahydrofuran / 24 h / 760 Torr

4.1: trifluoroacetic acid / CH₂Cl₂ / 12 h / 20 °C

5.1: 656 mg / triethylamine; DMAP / CH₂Cl₂ / 24 h / 20 °C

6.1: tetrahydrofuran; acetonitrile; H₂O / 0.25 h / 20 °C

6.2: 72 percent / NaCNBH₃; aq. acetic acid / tetrahydrofuran; acetonitrile / 0.75 h / 20 °C

With 1H-imidazole; dmap; hydrogen; iodine; sodium hexamethyldisilazane; triethylamine; triphenylphosphine; trifluoroacetic acid; Pd-BaSO₄; In tetrahydrofuran; dichloromethane; water; acetonitrile;
DOI:10.1021/ja0535918

Reference yield:

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

: 866110-60-3
(3S,5S,6R)-3-[5-(tert-Butyl-dimethyl-silanyloxy)-2,4-dimethoxy-3-methyl-benzyl]-4-methyl-5,6-diphenyl-morpholin-2-one

Guidance literature:: Multi-step reaction with 5 steps

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

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

2.1: H₂ / Pd/BaSO₄ / tetrahydrofuran / 24 h / 760 Torr

3.1: trifluoroacetic acid / CH₂Cl₂ / 12 h / 20 °C

4.1: 656 mg / triethylamine; DMAP / CH₂Cl₂ / 24 h / 20 °C

5.1: tetrahydrofuran; acetonitrile; H₂O / 0.25 h / 20 °C

5.2: 72 percent / NaCNBH₃; aq. acetic acid / tetrahydrofuran; acetonitrile / 0.75 h / 20 °C

With dmap; hydrogen; sodium hexamethyldisilazane; triethylamine; trifluoroacetic acid; Pd-BaSO₄; In tetrahydrofuran; dichloromethane; water; acetonitrile;
DOI:10.1021/ja0535918