(3S,5S)-5-{Allyl-[2-(tert-butyl-dimethyl-silanyloxy)-2-(3-methoxy-phenyl)-ethyl]-carbamoyl}-2-methoxy-3-methoxymethoxymethyl-pyrrolidine-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: (3S,5S)-5-{Allyl-[2-(tert-butyl-dimethyl-silanyloxy)-2-(3-methoxy-phenyl)-ethyl]-carbamoyl}-2-methoxy-3-methoxymethoxymethyl-pyrrolidine-1-carboxylic acid benzyl ester
• CAS No.: 129416-26-8
• Molecular Formula: C₃₅H₅₂N₂O₈Si
• Molecular Weight: 656.892

Synonyms:

Chemical Property of (3S,5S)-5-{Allyl-[2-(tert-butyl-dimethyl-silanyloxy)-2-(3-methoxy-phenyl)-ethyl]-carbamoyl}-2-methoxy-3-methoxymethoxymethyl-pyrrolidine-1-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,5S)-5-{Allyl-[2-(tert-butyl-dimethyl-silanyloxy)-2-(3-methoxy-phenyl)-ethyl]-carbamoyl}-2-methoxy-3-methoxymethoxymethyl-pyrrolidine-1-carboxylic acid benzyl ester

There total 13 articles about (3S,5S)-5-{Allyl-[2-(tert-butyl-dimethyl-silanyloxy)-2-(3-methoxy-phenyl)-ethyl]-carbamoyl}-2-methoxy-3-methoxymethoxymethyl-pyrrolidine-1-carboxylic 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:

2-amino-1-(3-methoxyphenyl)ethanol (27382-18-9) → (3S,5S)-5-{Allyl-[2-(tert-butyl-dimethyl-silanyloxy)-2-(3-methoxy-phenyl)-ethyl]-carbamoyl}-2-methoxy-3-methoxymethoxymethyl-pyrrolidine-1-carboxylic acid benzyl ester (129416-26-8)

Guidance literature:

Multi-step reaction with 11 steps

1: 93 percent / pyridine / CH₂Cl₂ / 0 °C

2: 90 percent / KH / tetrahydrofuran

3: 4 N NaOH / ethanol / Heating

4: DMAP, iPr₂NEt / CH₂Cl₂

5: 96 percent / NEt₃ / CH₂Cl₂ / 0 °C

6: tetrahydrofuran / 60 °C

7: 1 N HCl / tetrahydrofuran

8: 91 percent / sodium cyanoborohydride / ethanol; tetrahydrofuran; acetic acid / -20 deg C to room temperature

9: 88 percent / iPrNEt₂ / CH₂Cl₂

10: RedAl / tetrahydrofuran / -78 to -50 deg C

11: PPTS

With pyridine; hydrogenchloride; dmap; sodium hydroxide; N,N-diethyl-N-isopropylamine; pyridinium p-toluenesulfonate; potassium hydride; sodium cyanoborohydride; triethylamine; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; ethanol; dichloromethane; acetic acid;

DOI:10.1016/0040-4039(90)80083-X

Reference yield:

5-(3-Methoxy-phenyl)-oxazolidin-2-one (129416-01-9) → (3S,5S)-5-{Allyl-[2-(tert-butyl-dimethyl-silanyloxy)-2-(3-methoxy-phenyl)-ethyl]-carbamoyl}-2-methoxy-3-methoxymethoxymethyl-pyrrolidine-1-carboxylic acid benzyl ester (129416-26-8)

Guidance literature:

Multi-step reaction with 10 steps

1: 90 percent / KH / tetrahydrofuran

2: 4 N NaOH / ethanol / Heating

3: DMAP, iPr₂NEt / CH₂Cl₂

4: 96 percent / NEt₃ / CH₂Cl₂ / 0 °C

5: tetrahydrofuran / 60 °C

6: 1 N HCl / tetrahydrofuran

7: 91 percent / sodium cyanoborohydride / ethanol; tetrahydrofuran; acetic acid / -20 deg C to room temperature

8: 88 percent / iPrNEt₂ / CH₂Cl₂

9: RedAl / tetrahydrofuran / -78 to -50 deg C

10: PPTS

With hydrogenchloride; dmap; sodium hydroxide; N,N-diethyl-N-isopropylamine; pyridinium p-toluenesulfonate; potassium hydride; sodium cyanoborohydride; triethylamine; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; ethanol; dichloromethane; acetic acid;

DOI:10.1016/0040-4039(90)80083-X

Reference yield:

2-Allylamino-1-(3-methoxy-phenyl)-ethanol → (3S,5S)-5-{Allyl-[2-(tert-butyl-dimethyl-silanyloxy)-2-(3-methoxy-phenyl)-ethyl]-carbamoyl}-2-methoxy-3-methoxymethoxymethyl-pyrrolidine-1-carboxylic acid benzyl ester (129416-26-8)

Guidance literature:

Multi-step reaction with 8 steps

1: DMAP, iPr₂NEt / CH₂Cl₂

2: 96 percent / NEt₃ / CH₂Cl₂ / 0 °C

3: tetrahydrofuran / 60 °C

4: 1 N HCl / tetrahydrofuran

5: 91 percent / sodium cyanoborohydride / ethanol; tetrahydrofuran; acetic acid / -20 deg C to room temperature

6: 88 percent / iPrNEt₂ / CH₂Cl₂

7: RedAl / tetrahydrofuran / -78 to -50 deg C

8: PPTS

With hydrogenchloride; dmap; N,N-diethyl-N-isopropylamine; pyridinium p-toluenesulfonate; sodium cyanoborohydride; triethylamine; N-ethyl-N,N-diisopropylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; In tetrahydrofuran; ethanol; dichloromethane; acetic acid;

DOI:10.1016/0040-4039(90)80083-X

upstream raw materials:

2-amino-1-(3-methoxyphenyl)ethanol

5-(3-Methoxy-phenyl)-oxazolidin-2-one

(tert-Butyl-dimethyl-silanyloxy)-(3-methoxy-phenyl)-acetonitrile

3-Allyl-5-(3-methoxy-phenyl)-oxazolidin-2-one

Downstream raw materials:

(1S,4S,5R,6R)-6-Hydroxymethyl-4-(3-methoxy-benzyl)-3,8-diaza-bicyclo[3.2.1]octan-2-one

(1S,5R,6R)-3-Allyl-6-hydroxymethyl-4-(3-methoxy-benzoyl)-2-oxo-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid benzyl ester

(1S,5R,6R)-6-Methoxymethoxymethyl-4-[1-(3-methoxy-phenyl)-meth-(Z)-ylidene]-2-oxo-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid benzyl ester

(1S,5R,6R)-4-[Hydroxy-(3-methoxy-phenyl)-methyl]-6-methoxymethoxymethyl-2-oxo-3,8-diaza-bicyclo[3.2.1]octane-8-carboxylic acid benzyl ester

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