(2S,4R,5R)-4-{2-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-ethyl}-5-(3-oxo-propyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

Base Information

Chemical Name:(2S,4R,5R)-4-{2-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-ethyl}-5-(3-oxo-propyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester
CAS No.:607731-89-5
Molecular Formula:C₃₀H₄₉NO₆Si
Molecular Weight:547.808
Hs Code.:

(2S,4R,5R)-4-{2-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-ethyl}-5-(3-oxo-propyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

Synonyms:(2S,4R,5R)-4-{2-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-ethyl}-5-(3-oxo-propyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

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Chemical Property of (2S,4R,5R)-4-{2-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-ethyl}-5-(3-oxo-propyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

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Technology Process of (2S,4R,5R)-4-{2-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-ethyl}-5-(3-oxo-propyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

There total 8 articles about (2S,4R,5R)-4-{2-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-ethyl}-5-(3-oxo-propyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-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: 81.0%

: 607732-08-1
(2S,4R,5R)-4-{2-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-ethyl}-5-(3-hydroxy-propyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

: 607731-89-5
(2S,4R,5R)-4-{2-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-ethyl}-5-(3-oxo-propyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

Guidance literature:: With oxalyl dichloride; TEA; dimethyl sulfoxide; In dichloromethane; at -60 - 20 ℃; for 1h;
DOI:10.1016/S0040-4020(03)01018-4

Reference yield:

: 365973-11-1
(2S,4S)-4-Allyl-5-oxo-pyrrolidine-2-carboxylic acid methyl ester

: 607731-89-5
(2S,4R,5R)-4-{2-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-ethyl}-5-(3-oxo-propyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: 99 percent / sodium hydroxide / tetrahydrofuran; H₂O / 0.5 h / 20 °C

2.1: 99 percent / CH₂Cl₂ / 48 h / Heating

3.1: O₃ / methanol / 1.5 h / -60 °C

3.2: 80 percent / NaBH₄ / methanol

4.1: 98 percent / imidazole / dimethylformamide / 16 h

5.1: LiHMDS / tetrahydrofuran / 0.33 h / -50 °C

5.2: 80 percent / tetrahydrofuran / 0.33 h

6.1: lithium triethylborohydride / tetrahydrofuran / 3 h / -78 °C

7.1: 0.44 g / tert-butyldimethylsilyl triflate / CH₂Cl₂ / 1 h / -78 °C

8.1: 9-BBN / tetrahydrofuran / 3 h

8.2: 83 percent / sodium hydroxide; hydrogen peroxide / tetrahydrofuran; H₂O / 16 h / Heating

9.1: 81 percent / oxalyl chloride; TEA; DMSO / CH₂Cl₂ / 1 h / -60 - 20 °C

With 1H-imidazole; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; TEA; t-butyldimethylsiyl triflate; lithium triethylborohydride; ozone; dimethyl sulfoxide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; 9.1: Swern oxidation;
DOI:10.1016/S0040-4020(03)01018-4

Reference yield:

: 237421-63-5
tert-butyl (2S,4R)-4-(prop-2-enyl)-pyroglutamate

: 607731-89-5
(2S,4R,5R)-4-{2-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-ethyl}-5-(3-oxo-propyl)-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: O₃ / methanol / 1.5 h / -60 °C

1.2: 80 percent / NaBH₄ / methanol

2.1: 98 percent / imidazole / dimethylformamide / 16 h

3.1: LiHMDS / tetrahydrofuran / 0.33 h / -50 °C

3.2: 80 percent / tetrahydrofuran / 0.33 h

4.1: lithium triethylborohydride / tetrahydrofuran / 3 h / -78 °C

5.1: 0.44 g / tert-butyldimethylsilyl triflate / CH₂Cl₂ / 1 h / -78 °C

6.1: 9-BBN / tetrahydrofuran / 3 h

6.2: 83 percent / sodium hydroxide; hydrogen peroxide / tetrahydrofuran; H₂O / 16 h / Heating

7.1: 81 percent / oxalyl chloride; TEA; DMSO / CH₂Cl₂ / 1 h / -60 - 20 °C

With 1H-imidazole; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; TEA; t-butyldimethylsiyl triflate; lithium triethylborohydride; ozone; dimethyl sulfoxide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 7.1: Swern oxidation;
DOI:10.1016/S0040-4020(03)01018-4