(S)-(-)-N-[1-(tert-butyldiphenylsilyloxymethyl)-2-(3,4-dimethoxyphenyl)ethyl]-4-oxopentanamide

Base Information

Chemical Name:(S)-(-)-N-[1-(tert-butyldiphenylsilyloxymethyl)-2-(3,4-dimethoxyphenyl)ethyl]-4-oxopentanamide
CAS No.:862819-80-5
Molecular Formula:C₃₂H₄₁NO₅Si
Molecular Weight:547.767
Hs Code.:

Synonyms:(S)-(-)-N-[1-(tert-butyldiphenylsilyloxymethyl)-2-(3,4-dimethoxyphenyl)ethyl]-4-oxopentanamide

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Chemical Property of (S)-(-)-N-[1-(tert-butyldiphenylsilyloxymethyl)-2-(3,4-dimethoxyphenyl)ethyl]-4-oxopentanamide

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Technology Process of (S)-(-)-N-[1-(tert-butyldiphenylsilyloxymethyl)-2-(3,4-dimethoxyphenyl)ethyl]-4-oxopentanamide

There total 8 articles about (S)-(-)-N-[1-(tert-butyldiphenylsilyloxymethyl)-2-(3,4-dimethoxyphenyl)ethyl]-4-oxopentanamide 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: 76.0%

: 917-54-4
methyllithium

: 336607-98-8
(S)-(-)-1-[1-(tert-butyldiphenylsilyloxymethyl)-2-(3,4-dimethoxyphenyl)ethyl]pyrrolidine-2,5-dione

: 862819-80-5
(S)-(-)-N-[1-(tert-butyldiphenylsilyloxymethyl)-2-(3,4-dimethoxyphenyl)ethyl]-4-oxopentanamide

Guidance literature:: In pentane; at -78 ℃; for 6h;
DOI:10.1021/jo051584w

Reference yield:

: 32161-30-1
(S)-3,4-dimethoxyphenylalanine

: 862819-80-5
(S)-(-)-N-[1-(tert-butyldiphenylsilyloxymethyl)-2-(3,4-dimethoxyphenyl)ethyl]-4-oxopentanamide

Guidance literature:: Multi-step reaction with 7 steps

2.1: 92 percent

3.1: 87 percent / LiAlH₄

4.1: 95 percent

5.1: 86 percent / TFA

6.2: 75 percent / Ac₂O; NaOAc

7.1: tetrahydrofuran; diethyl ether / 6 h / -78 °C

With lithium aluminium tetrahydride; trifluoroacetic acid; In tetrahydrofuran; diethyl ether;
DOI:10.1016/S0040-4039(00)02319-4

Reference yield:

: 138908-56-2
(S)-(+)-2-tert-butoxycarbonylamino-3-(3,4-dimethoxyphenyl)propionic acid methyl ester

: 862819-80-5
(S)-(-)-N-[1-(tert-butyldiphenylsilyloxymethyl)-2-(3,4-dimethoxyphenyl)ethyl]-4-oxopentanamide

Guidance literature:: Multi-step reaction with 6 steps

1: 87 percent / LiAlH₄ / diethyl ether; tetrahydrofuran / 0.5 h / Heating

2: 95 percent / imidazole / CH₂Cl₂ / 18 h / 20 °C

3: 86 percent / CF₃CO₂H / CH₂Cl₂ / 1 h / 20 °C

4: diethyl ether / 16 h / Heating

5: 3.9 g / NaOAc; Ac₂O / 1 h / 85 °C

6: 76 percent / pentane / 6 h / -78 °C

With 1H-imidazole; lithium aluminium tetrahydride; sodium acetate; acetic anhydride; trifluoroacetic acid; In tetrahydrofuran; diethyl ether; dichloromethane; pentane;
DOI:10.1021/jo051584w