tert-butyl (S)-2-(diphenylmethyleneamino)-3-[3-(triisopropylsilyloxy)phenyl]propanoate

Base Information

Chemical Name:tert-butyl (S)-2-(diphenylmethyleneamino)-3-[3-(triisopropylsilyloxy)phenyl]propanoate
CAS No.:1425924-23-7
Molecular Formula:C₃₅H₄₇NO₃Si
Molecular Weight:557.849
Hs Code.:

Synonyms:tert-butyl (S)-2-(diphenylmethyleneamino)-3-[3-(triisopropylsilyloxy)phenyl]propanoate

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Chemical Property of tert-butyl (S)-2-(diphenylmethyleneamino)-3-[3-(triisopropylsilyloxy)phenyl]propanoate

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Technology Process of tert-butyl (S)-2-(diphenylmethyleneamino)-3-[3-(triisopropylsilyloxy)phenyl]propanoate

There total 5 articles about tert-butyl (S)-2-(diphenylmethyleneamino)-3-[3-(triisopropylsilyloxy)phenyl]propanoate 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: 82.0%

: 1425924-22-6
[3-(iodomethyl)phenoxy]triisopropylsilane

: 81477-94-3
N-(diphenylmethylene)glycine tert-butyl ester

: 1425924-23-7
tert-butyl (S)-2-(diphenylmethyleneamino)-3-[3-(triisopropylsilyloxy)phenyl]propanoate

Guidance literature:: [3-(iodomethyl)phenoxy]triisopropylsilane; N-(diphenylmethylene)glycine tert-butyl ester; With O-allyl-N-[(1-naphthyl)methyl]cinchonidinium bromide; In dichloromethane; toluene; at -10 ℃;

With water; potassium hydroxide; In dichloromethane; toluene; at -5 ℃; for 33h; enantioselective reaction;
DOI:10.1021/jo3027214

Reference yield:

: 100-83-4
meta-hydroxybenzaldehyde

: 1425924-23-7
tert-butyl (S)-2-(diphenylmethyleneamino)-3-[3-(triisopropylsilyloxy)phenyl]propanoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 10 h / -50 - 20 °C / Inert atmosphere

2.1: sodium tetrahydroborate / methanol / 0.67 h / 20 °C / Inert atmosphere

3.1: 1H-imidazole; triphenylphosphine; iodine / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

4.1: O-allyl-N-[(1-naphthyl)methyl]cinchonidinium bromide / dichloromethane; toluene / -10 °C

4.2: 33 h / -5 °C

With 1H-imidazole; sodium tetrahydroborate; O-allyl-N-[(1-naphthyl)methyl]cinchonidinium bromide; iodine; triphenylphosphine; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo3027214

Reference yield:

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 1425924-23-7
tert-butyl (S)-2-(diphenylmethyleneamino)-3-[3-(triisopropylsilyloxy)phenyl]propanoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 10 h / -50 - 20 °C / Inert atmosphere

2.1: sodium tetrahydroborate / methanol / 0.67 h / 20 °C / Inert atmosphere

3.1: 1H-imidazole; triphenylphosphine; iodine / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

4.1: O-allyl-N-[(1-naphthyl)methyl]cinchonidinium bromide / dichloromethane; toluene / -10 °C

4.2: 33 h / -5 °C

With 1H-imidazole; sodium tetrahydroborate; O-allyl-N-[(1-naphthyl)methyl]cinchonidinium bromide; iodine; triphenylphosphine; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo3027214