(2S,4R)-4-[(triisopropylsilyl)oxy]-1,2-pyrrolidinedicarboxylic acid 1-tert-butyl ester 2-methyl ester

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Chemical Name:(2S,4R)-4-[(triisopropylsilyl)oxy]-1,2-pyrrolidinedicarboxylic acid 1-tert-butyl ester 2-methyl ester
CAS No.:946435-41-2
Molecular Formula:C₂₀H₃₉NO₅Si
Molecular Weight:401.619
Hs Code.:

Synonyms:(2S,4R)-4-[(triisopropylsilyl)oxy]-1,2-pyrrolidinedicarboxylic acid 1-tert-butyl ester 2-methyl ester

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Chemical Property of (2S,4R)-4-[(triisopropylsilyl)oxy]-1,2-pyrrolidinedicarboxylic acid 1-tert-butyl ester 2-methyl ester

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Technology Process of (2S,4R)-4-[(triisopropylsilyl)oxy]-1,2-pyrrolidinedicarboxylic acid 1-tert-butyl ester 2-methyl ester

There total 1 articles about (2S,4R)-4-[(triisopropylsilyl)oxy]-1,2-pyrrolidinedicarboxylic acid 1-tert-butyl ester 2-methyl 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

: 946435-41-2
(2S,4R)-4-[(triisopropylsilyl)oxy]-1,2-pyrrolidinedicarboxylic acid 1-tert-butyl ester 2-methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: Et₃N / CH₂Cl₂ / 2.33 h / 0 - 20 °C

2: 94 percent / imidazole / CH₂Cl₂ / 48 h

With 1H-imidazole; triethylamine; In dichloromethane;
DOI:10.1021/ol071147z

Reference yield:

: 946435-41-2
(2S,4R)-4-[(triisopropylsilyl)oxy]-1,2-pyrrolidinedicarboxylic acid 1-tert-butyl ester 2-methyl ester

: 946435-50-3
(2S)-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 10 steps

1: 91 percent / NaBH₄; CaCl₂ / tetrahydrofuran; ethanol / 0 °C

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

3: 63 percent / t-BuLi / pentane; tetrahydrofuran / 2 h / -78 °C

4: 83 percent / i-Pr₂NEt; Bu₄NI / tetrahydrofuran / 20 h / Heating

5: 98 percent / ethyl acetate; H₂O / 0.25 h

6: 98 percent / LiAlH₄ / diethyl ether / 0.33 h / 0 °C

7: 80 percent / pyridine; DMAP / CH₂Cl₂ / 3.5 h

8: 95 percent / Bu₄NF; AcOH / tetrahydrofuran / 2 h

9: 40 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂ / 1 h / -78 °C

10: 62 percent / K₂CO₃ / methanol; H₂O / 0.5 h

With pyridine; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; tetrabutyl ammonium fluoride; tert.-butyl lithium; tetra-(n-butyl)ammonium iodide; potassium carbonate; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; calcium chloride; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; pentane; 2: Swern oxidation / 9: Swern oxidation;
DOI:10.1021/ol071147z

Reference yield:

: 946435-41-2
(2S,4R)-4-[(triisopropylsilyl)oxy]-1,2-pyrrolidinedicarboxylic acid 1-tert-butyl ester 2-methyl 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 11 steps

1: 91 percent / NaBH₄; CaCl₂ / tetrahydrofuran; ethanol / 0 °C

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

3: 63 percent / t-BuLi / pentane; tetrahydrofuran / 2 h / -78 °C

4: 83 percent / i-Pr₂NEt; Bu₄NI / tetrahydrofuran / 20 h / Heating

5: 98 percent / ethyl acetate; H₂O / 0.25 h

6: 98 percent / LiAlH₄ / diethyl ether / 0.33 h / 0 °C

7: 80 percent / pyridine; DMAP / CH₂Cl₂ / 3.5 h

8: 95 percent / Bu₄NF; AcOH / tetrahydrofuran / 2 h

9: 40 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂ / 1 h / -78 °C

10: 62 percent / K₂CO₃ / methanol; H₂O / 0.5 h

11: 67 percent / tetrahydrofuran / 24 h / Heating

With pyridine; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; tetrabutyl ammonium fluoride; tert.-butyl lithium; tetra-(n-butyl)ammonium iodide; potassium carbonate; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; calcium chloride; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; ethyl acetate; pentane; 2: Swern oxidation / 9: Swern oxidation;
DOI:10.1021/ol071147z