(3S,5S,6R)-3-(3-Hydroxy-4-methoxy-5-methyl-benzyl)-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (3S,5S,6R)-3-(3-Hydroxy-4-methoxy-5-methyl-benzyl)-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid tert-butyl ester
• CAS No.: 575444-15-4
• Molecular Formula: C₃₀H₃₃NO₆
• Molecular Weight: 503.595

Synonyms:(3S,5S,6R)-3-(3-Hydroxy-4-methoxy-5-methyl-benzyl)-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid tert-butyl ester

Chemical Property of (3S,5S,6R)-3-(3-Hydroxy-4-methoxy-5-methyl-benzyl)-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

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Technology Process of (3S,5S,6R)-3-(3-Hydroxy-4-methoxy-5-methyl-benzyl)-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid tert-butyl ester

There total 9 articles about (3S,5S,6R)-3-(3-Hydroxy-4-methoxy-5-methyl-benzyl)-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid tert-butyl 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: 95.0%

(3S,5S,6R)-3-(3-Benzyloxy-4-methoxy-5-methyl-benzyl)-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid tert-butyl ester (575444-11-0) → (3S,5S,6R)-3-(3-Hydroxy-4-methoxy-5-methyl-benzyl)-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid tert-butyl ester (575444-15-4)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; under 760 Torr;

DOI:10.1016/S0040-4039(03)01082-7

Reference yield:

3,4-dihydroxy-5-methylbenzaldehyde (82628-68-0) → (3S,5S,6R)-3-(3-Hydroxy-4-methoxy-5-methyl-benzyl)-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid tert-butyl ester (575444-15-4)

Guidance literature:

Multi-step reaction with 8 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

With lithium aluminium tetrahydride; carbon tetrabromide; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; potassium carbonate; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4039(03)01082-7

Reference yield:

vanillin (121-33-5,8014-42-4) → (3S,5S,6R)-3-(3-Hydroxy-4-methoxy-5-methyl-benzyl)-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid tert-butyl ester (575444-15-4)

Guidance literature:

Multi-step reaction with 9 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

With lithium aluminium tetrahydride; carbon tetrabromide; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; potassium carbonate; dimethyl amine; triethylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4039(03)01082-7

upstream raw materials:

(3S,5S,6R)-3-(3-Benzyloxy-4-methoxy-5-methyl-benzyl)-2-oxo-5,6-diphenyl-morpholine-4-carboxylic acid tert-butyl ester

3,4-dihydroxy-5-methylbenzaldehyde

vanillin

3-hydroxy-4-methoxy-5-methylbenzaldehyde

Downstream raw materials:

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

3-[3-(tert-butyl-dimethyl-silanyloxy)-4-methoxy-5-methyl-phenyl]-2-[(9H-fluoren-9-ylmethoxycarbonyl)-methyl-amino]-propionic acid

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

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

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