(S)-{2-[(S)-2-(benzyloxycarbonylamino)-3-(methyl)butanamido]-3-[3-(triisopropylsilyloxy)phenyl]}propanoic acid

Base Information

Chemical Name:(S)-{2-[(S)-2-(benzyloxycarbonylamino)-3-(methyl)butanamido]-3-[3-(triisopropylsilyloxy)phenyl]}propanoic acid
CAS No.:1425924-28-2
Molecular Formula:C₃₁H₄₆N₂O₆Si
Molecular Weight:570.802
Hs Code.:

Synonyms:(S)-{2-[(S)-2-(benzyloxycarbonylamino)-3-(methyl)butanamido]-3-[3-(triisopropylsilyloxy)phenyl]}propanoic acid

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Chemical Property of (S)-{2-[(S)-2-(benzyloxycarbonylamino)-3-(methyl)butanamido]-3-[3-(triisopropylsilyloxy)phenyl]}propanoic acid

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Technology Process of (S)-{2-[(S)-2-(benzyloxycarbonylamino)-3-(methyl)butanamido]-3-[3-(triisopropylsilyloxy)phenyl]}propanoic acid

There total 8 articles about (S)-{2-[(S)-2-(benzyloxycarbonylamino)-3-(methyl)butanamido]-3-[3-(triisopropylsilyloxy)phenyl]}propanoic acid 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: 77.0%

: 1425924-27-1
tert-butyl (S)-{2-[(S)-2-(benzyloxycarbonylamino)-3-(methyl)butanamido]-3-[3-(triisopropylsilyloxy)phenyl]}propanoate

: 1425924-28-2
(S)-{2-[(S)-2-(benzyloxycarbonylamino)-3-(methyl)butanamido]-3-[3-(triisopropylsilyloxy)phenyl]}propanoic acid

Guidance literature:: With methoxybenzene; trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; chemoselective reaction; Inert atmosphere;
DOI:10.1021/jo3027214

Reference yield:

: 1425924-25-9
tert-butyl (S)-2-amino-3-[3-(triisopropylsilyloxy)phenyl]propanoate

: 1425924-28-2
(S)-{2-[(S)-2-(benzyloxycarbonylamino)-3-(methyl)butanamido]-3-[3-(triisopropylsilyloxy)phenyl]}propanoic acid

Guidance literature:: Multi-step reaction with 2 steps

1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.75 h / 20 °C / Inert atmosphere

2: methoxybenzene; trifluoroacetic acid / dichloromethane / 0 - 20 °C / Inert atmosphere

With methoxybenzene; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo3027214

Reference yield:

: 100-83-4
meta-hydroxybenzaldehyde

: 1425924-28-2
(S)-{2-[(S)-2-(benzyloxycarbonylamino)-3-(methyl)butanamido]-3-[3-(triisopropylsilyloxy)phenyl]}propanoic acid

Guidance literature:: Multi-step reaction with 7 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

5.1: water; acetic acid / tetrahydrofuran / 6 h / 20 °C

5.2: 0 °C / Neutral conditions

6.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.75 h / 20 °C / Inert atmosphere

7.1: methoxybenzene; trifluoroacetic acid / dichloromethane / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; sodium tetrahydroborate; O-allyl-N-[(1-naphthyl)methyl]cinchonidinium bromide; water; iodine; acetic acid; methoxybenzene; N-ethyl-N,N-diisopropylamine; triphenylphosphine; HATU; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo3027214