(2S,4R)-2-[(2Z)-3-ethoxy-1-[(2-methoxyethoxy)methoxy]allyl]-4-[(triisopropylsilyl)oxy]pyrrolidine-1-carboxylic acid tert-butyl ester

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Chemical Name:(2S,4R)-2-[(2Z)-3-ethoxy-1-[(2-methoxyethoxy)methoxy]allyl]-4-[(triisopropylsilyl)oxy]pyrrolidine-1-carboxylic acid tert-butyl ester
CAS No.:946435-44-5
Molecular Formula:C₂₇H₅₃NO₇Si
Molecular Weight:531.806
Hs Code.:

Synonyms:(2S,4R)-2-[(2Z)-3-ethoxy-1-[(2-methoxyethoxy)methoxy]allyl]-4-[(triisopropylsilyl)oxy]pyrrolidine-1-carboxylic acid tert-butyl ester

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Chemical Property of (2S,4R)-2-[(2Z)-3-ethoxy-1-[(2-methoxyethoxy)methoxy]allyl]-4-[(triisopropylsilyl)oxy]pyrrolidine-1-carboxylic acid tert-butyl ester

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Technology Process of (2S,4R)-2-[(2Z)-3-ethoxy-1-[(2-methoxyethoxy)methoxy]allyl]-4-[(triisopropylsilyl)oxy]pyrrolidine-1-carboxylic acid tert-butyl ester

There total 1 articles about (2S,4R)-2-[(2Z)-3-ethoxy-1-[(2-methoxyethoxy)methoxy]allyl]-4-[(triisopropylsilyl)oxy]pyrrolidine-1-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:

: 40216-83-9
L-4-hydroxyproline methyl ester hydrochloride

: 946435-44-5
(2S,4R)-2-[(2Z)-3-ethoxy-1-[(2-methoxyethoxy)methoxy]allyl]-4-[(triisopropylsilyl)oxy]pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: Et₃N / CH₂Cl₂ / 2.33 h / 0 - 20 °C

2: 94 percent / imidazole / CH₂Cl₂ / 48 h

3: 91 percent / NaBH₄; CaCl₂ / tetrahydrofuran; ethanol / 0 °C

4: 91 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.83 h / -78 - 20 °C

5: 63 percent / t-BuLi / pentane; tetrahydrofuran / 2 h / -78 °C

6: 83 percent / i-Pr₂NEt; Bu₄NI / tetrahydrofuran / 20 h / Heating

With 1H-imidazole; sodium tetrahydroborate; oxalyl dichloride; tert.-butyl lithium; tetra-(n-butyl)ammonium iodide; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; calcium chloride; In tetrahydrofuran; ethanol; dichloromethane; pentane; 4: Swern oxidation;
DOI:10.1021/ol071147z

Reference yield: 98.0%

: 946435-44-5
(2S,4R)-2-[(2Z)-3-ethoxy-1-[(2-methoxyethoxy)methoxy]allyl]-4-[(triisopropylsilyl)oxy]pyrrolidine-1-carboxylic acid tert-butyl ester

: 5707-04-0
Phenylselenyl chloride

: 946435-45-6
(2S,4R)-2-[1-[(2-methoxyethoxy)methoxy]-3-oxo-2-(phenylselanyl)propyl]-4-[(triisopropylsilyl)oxy]pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: In water; ethyl acetate; for 0.25h;
DOI:10.1021/ol071147z

Reference yield:

: 946435-44-5
(2S,4R)-2-[(2Z)-3-ethoxy-1-[(2-methoxyethoxy)methoxy]allyl]-4-[(triisopropylsilyl)oxy]pyrrolidine-1-carboxylic acid tert-butyl ester

: (2S)-3-dimethylaminomethylene-2-[(1R)-3-hydroxy-1-[(2-methoxyethoxy)methoxy]-2-(phenylselanyl)propyl]-4-oxopyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 98 percent / ethyl acetate; H₂O / 0.25 h

2: 98 percent / LiAlH₄ / diethyl ether / 0.33 h / 0 °C

3: 80 percent / pyridine; DMAP / CH₂Cl₂ / 3.5 h

4: 95 percent / Bu₄NF; AcOH / tetrahydrofuran / 2 h

5: 40 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂ / 1 h / -78 °C

6: 62 percent / K₂CO₃ / methanol; H₂O / 0.5 h

7: 67 percent / tetrahydrofuran / 24 h / Heating

With pyridine; dmap; lithium aluminium tetrahydride; oxalyl dichloride; tetrabutyl ammonium fluoride; potassium carbonate; acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; ethyl acetate; 5: Swern oxidation;
DOI:10.1021/ol071147z