(S)-1-((R)-2-Benzyloxycarbonyloxy-4-methyl-4-triethylsilanyloxy-pentanoyl)-pyrrolidine-2-carboxylic acid

Base Information

Chemical Name:(S)-1-((R)-2-Benzyloxycarbonyloxy-4-methyl-4-triethylsilanyloxy-pentanoyl)-pyrrolidine-2-carboxylic acid
CAS No.:383397-45-3
Molecular Formula:C₂₅H₃₉NO₇Si
Molecular Weight:493.673
Hs Code.:

Synonyms:(S)-1-((R)-2-Benzyloxycarbonyloxy-4-methyl-4-triethylsilanyloxy-pentanoyl)-pyrrolidine-2-carboxylic acid

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Chemical Property of (S)-1-((R)-2-Benzyloxycarbonyloxy-4-methyl-4-triethylsilanyloxy-pentanoyl)-pyrrolidine-2-carboxylic acid

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Technology Process of (S)-1-((R)-2-Benzyloxycarbonyloxy-4-methyl-4-triethylsilanyloxy-pentanoyl)-pyrrolidine-2-carboxylic acid

There total 10 articles about (S)-1-((R)-2-Benzyloxycarbonyloxy-4-methyl-4-triethylsilanyloxy-pentanoyl)-pyrrolidine-2-carboxylic 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: 99.0%

: 383397-43-1
(S)-1-((R)-2-Benzyloxycarbonyloxy-4-methyl-4-triethylsilanyloxy-pentanoyl)-pyrrolidine-2-carboxylic acid allyl ester

: 383397-45-3
(S)-1-((R)-2-Benzyloxycarbonyloxy-4-methyl-4-triethylsilanyloxy-pentanoyl)-pyrrolidine-2-carboxylic acid

Guidance literature:: With morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾;
DOI:10.1021/jo015953+

Reference yield:

: 3123-97-5
dihydro-5,5-dimethyl-2(3H)-furanone

: 383397-45-3
(S)-1-((R)-2-Benzyloxycarbonyloxy-4-methyl-4-triethylsilanyloxy-pentanoyl)-pyrrolidine-2-carboxylic acid

Guidance literature:: Multi-step reaction with 10 steps

1: aq. NaOH / ethanol / 2 h / Heating

2: 3.05 g / diethyl ether / 2 h / 0 °C

3: 90 percent / 2,6-lutidine / CH₂Cl₂ / 14.5 h / 0 - 20 °C

4: 91 percent / LiOH*H₂O / H₂O; tetrahydrofuran; methanol / 3.25 h / 0 - 20 °C

5: Et₃N / tetrahydrofuran / 1 h / -78 - 0 °C

6: 1.03 percent / Et₃N; DMAP / tetrahydrofuran / 14 h / 20 °C

7: 99 percent / DMAP / CH₂Cl₂ / 4 h / 20 °C

8: 91 percent / LiOH; aq. H₂O₂ / tetrahydrofuran / 1.25 h / 0 °C

9: 80 percent / DCC; HOBt

10: 99 percent / Pd(PPh₃)4; morpholine

With morpholine; 2,6-dimethylpyridine; dmap; lithium hydroxide; sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; dihydrogen peroxide; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water;
DOI:10.1021/jo015953+

Reference yield:

: 23327-19-7
4-hydroxy-4-methyl-valeric acid

: 383397-45-3
(S)-1-((R)-2-Benzyloxycarbonyloxy-4-methyl-4-triethylsilanyloxy-pentanoyl)-pyrrolidine-2-carboxylic acid

Guidance literature:: Multi-step reaction with 9 steps

1: 3.05 g / diethyl ether / 2 h / 0 °C

2: 90 percent / 2,6-lutidine / CH₂Cl₂ / 14.5 h / 0 - 20 °C

3: 91 percent / LiOH*H₂O / H₂O; tetrahydrofuran; methanol / 3.25 h / 0 - 20 °C

4: Et₃N / tetrahydrofuran / 1 h / -78 - 0 °C

5: 1.03 percent / Et₃N; DMAP / tetrahydrofuran / 14 h / 20 °C

6: 99 percent / DMAP / CH₂Cl₂ / 4 h / 20 °C

7: 91 percent / LiOH; aq. H₂O₂ / tetrahydrofuran / 1.25 h / 0 °C

8: 80 percent / DCC; HOBt

9: 99 percent / Pd(PPh₃)4; morpholine

With morpholine; 2,6-dimethylpyridine; dmap; lithium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; dihydrogen peroxide; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water;
DOI:10.1021/jo015953+