(2S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-((S)-1-carboxy-ethylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(2S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-((S)-1-carboxy-ethylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester
CAS No.:177607-89-5
Molecular Formula:C₁₉H₃₆N₂O₆Si
Molecular Weight:416.59
Hs Code.:

Synonyms:(2S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-((S)-1-carboxy-ethylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

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Chemical Property of (2S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-((S)-1-carboxy-ethylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

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Technology Process of (2S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-((S)-1-carboxy-ethylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 1 articles about (2S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-((S)-1-carboxy-ethylcarbamoyl)-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:

: 87691-27-8,946610-68-0
N-tert-butoxycarbonyl-L-cis-4-hydroxyproline

: 177607-89-5
(2S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-((S)-1-carboxy-ethylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: BOP-Cl, Et₃N / CH₂Cl₂ / 80 h / 25 °C

2: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0 deg C, 15 min; 25 deg C, 15 min

3: 90 percent / H₂ / Pd/C / methanol / 2 h

With 2,6-dimethylpyridine; hydrogen; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; triethylamine; palladium on activated charcoal; In methanol; dichloromethane;
DOI:10.1021/jo952123l

Reference yield:

: 177607-89-5
(2S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-((S)-1-carboxy-ethylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

: 141205-31-4
microcolin A

Guidance literature:: Multi-step reaction with 9 steps

1: 98 percent / DMAP, isopropenyl chloroformate / CH₂Cl₂ / 2 h / -5 °C

2: 97 percent / acetonitrile / 2.5 h / Heating

3: 73 percent / NaBH₄ / acetic acid; CH₂Cl₂ / 4.5 h / 0 °C

4: Et₃N / CH₂Cl₂ / 1 h / 25 °C

5: 1,8-diazabicyclo<5.4.0>undec-7-ene, Et₃N / CH₂Cl₂ / 0.33 h

6: 97 percent / 4N HCl / dioxane / 2 h / 0 °C

7: 50 percent / BOP-Cl, Et₃N / CH₂Cl₂ / 25 °C

8: 98 percent / 4N HCl / dioxane / 4 h / 0 °C

9: 56 percent / BOP-Cl, Et₃N / CH₂Cl₂ / 25 °C

With hydrogenchloride; dmap; sodium tetrahydroborate; Isopropenyl chloroformate; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In 1,4-dioxane; dichloromethane; acetic acid; acetonitrile;
DOI:10.1021/jo952123l

Reference yield:

: 177607-89-5
(2S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-((S)-1-carboxy-ethylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

: C₃₉H₆₅N₅O₉

Guidance literature:: Multi-step reaction with 9 steps

1: 98 percent / DMAP, isopropenyl chloroformate / CH₂Cl₂ / 2 h / -5 °C

2: 97 percent / acetonitrile / 2.5 h / Heating

3: 73 percent / NaBH₄ / acetic acid; CH₂Cl₂ / 4.5 h / 0 °C

4: Et₃N / CH₂Cl₂ / 1 h / 25 °C

5: 1,8-diazabicyclo<5.4.0>undec-7-ene, Et₃N / CH₂Cl₂ / 0.33 h

6: 97 percent / 4N HCl / dioxane / 2 h / 0 °C

7: 50 percent / BOP-Cl, Et₃N / CH₂Cl₂ / 25 °C

8: 98 percent / 4N HCl / dioxane / 4 h / 0 °C

9: BOP-Cl, Et₃N / CH₂Cl₂ / 25 °C

With hydrogenchloride; dmap; sodium tetrahydroborate; Isopropenyl chloroformate; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In 1,4-dioxane; dichloromethane; acetic acid; acetonitrile;
DOI:10.1021/jo952123l