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

Base Information

Chemical Name:(3S,5S,6R)-3-[3-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-5-methyl-benzyl]-5,6-diphenyl-morpholin-2-one
CAS No.:575444-17-6
Molecular Formula:C₃₁H₃₉NO₄Si
Molecular Weight:517.74
Hs Code.:

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

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

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

There total 12 articles about (3S,5S,6R)-3-[3-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-5-methyl-benzyl]-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: 93.0%

: 575444-16-5
3-[3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-5-methyl-benzyl]-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid tert-butyl ester

: 575444-17-6
(3S,5S,6R)-3-[3-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-5-methyl-benzyl]-5,6-diphenyl-morpholin-2-one

Guidance literature:: With trifluoroacetic acid; In dichloromethane;
DOI:10.1016/S0040-4039(03)01082-7

Reference yield:

: 82628-68-0
3,4-dihydroxy-5-methylbenzaldehyde

: 575444-17-6
(3S,5S,6R)-3-[3-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-5-methyl-benzyl]-5,6-diphenyl-morpholin-2-one

Guidance literature:: Multi-step reaction with 10 steps

1: 82 percent / Et₃N / dimethylformamide

2: 88 percent / K₂CO₃ / acetone

3: 82 percent / TBAF / tetrahydrofuran

4: 86 percent / K₂CO₃ / acetone

5: 100 percent / LiAlH₄ / diethyl ether

6: 94 percent / CBr₄; Ph₃P / tetrahydrofuran

7: NaHDMS / tetrahydrofuran / -78 °C

8: 95 percent / hydrrogen / Pd/C / ethanol / 760 Torr

9: 82 percent / DMAP; Et₃N / CH₂Cl₂

10: 93 percent / TFA / CH₂Cl₂

With dmap; lithium aluminium tetrahydride; carbon tetrabromide; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; potassium carbonate; triethylamine; triphenylphosphine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0040-4039(03)01082-7

Reference yield:

: 121-33-5,8014-42-4
vanillin

: 575444-17-6
(3S,5S,6R)-3-[3-(tert-Butyl-dimethyl-silanyloxy)-4-methoxy-5-methyl-benzyl]-5,6-diphenyl-morpholin-2-one

Guidance literature:: Multi-step reaction with 11 steps

1.1: Me₂NH / ethanol

1.2: conc. HCl; SnCl₂

1.3: AlCl₃; pyridine / CH₂Cl₂

2.1: 82 percent / Et₃N / dimethylformamide

3.1: 88 percent / K₂CO₃ / acetone

4.1: 82 percent / TBAF / tetrahydrofuran

5.1: 86 percent / K₂CO₃ / acetone

6.1: 100 percent / LiAlH₄ / diethyl ether

7.1: 94 percent / CBr₄; Ph₃P / tetrahydrofuran

8.1: NaHDMS / tetrahydrofuran / -78 °C

9.1: 95 percent / hydrrogen / Pd/C / ethanol / 760 Torr

10.1: 82 percent / DMAP; Et₃N / CH₂Cl₂

11.1: 93 percent / TFA / CH₂Cl₂

With dmap; lithium aluminium tetrahydride; carbon tetrabromide; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; potassium carbonate; dimethyl amine; triethylamine; triphenylphosphine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1016/S0040-4039(03)01082-7