(2S,3R)-3-{4-[2-((2S,3S)-2-Amino-3-methyl-pentanoylamino)-1-triisopropylsilanyloxy-ethyl]-phenoxy}-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

Base Information

Chemical Name:(2S,3R)-3-{4-[2-((2S,3S)-2-Amino-3-methyl-pentanoylamino)-1-triisopropylsilanyloxy-ethyl]-phenoxy}-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester
CAS No.:540508-57-4
Molecular Formula:C₃₃H₅₇N₃O₇Si
Molecular Weight:635.917
Hs Code.:

(2S,3R)-3-{4-[2-((2S,3S)-2-Amino-3-methyl-pentanoylamino)-1-triisopropylsilanyloxy-ethyl]-phenoxy}-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

Synonyms:(2S,3R)-3-{4-[2-((2S,3S)-2-Amino-3-methyl-pentanoylamino)-1-triisopropylsilanyloxy-ethyl]-phenoxy}-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

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Chemical Property of (2S,3R)-3-{4-[2-((2S,3S)-2-Amino-3-methyl-pentanoylamino)-1-triisopropylsilanyloxy-ethyl]-phenoxy}-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

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Technology Process of (2S,3R)-3-{4-[2-((2S,3S)-2-Amino-3-methyl-pentanoylamino)-1-triisopropylsilanyloxy-ethyl]-phenoxy}-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

There total 10 articles about (2S,3R)-3-{4-[2-((2S,3S)-2-Amino-3-methyl-pentanoylamino)-1-triisopropylsilanyloxy-ethyl]-phenoxy}-pyrrolidine-1,2-dicarboxylic acid 1-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: 87.0%

: 540508-53-0
(2S,3R)-3-{4-[2-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylamino)-1-triisopropylsilanyloxy-ethyl]-phenoxy}-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

: 540508-57-4
(2S,3R)-3-{4-[2-((2S,3S)-2-Amino-3-methyl-pentanoylamino)-1-triisopropylsilanyloxy-ethyl]-phenoxy}-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

Guidance literature:: With methanol; palladium on activated charcoal; at 20 ℃; for 1h;
DOI:10.1016/S0040-4039(03)00278-8

Reference yield:

: 128836-20-4
tert-butyl (2R,3R)-2-[(tert-butyldimethylsiloxy)methyl]-3-hydroxypyrrolidine-1-carboxylate

: 540508-57-4
(2S,3R)-3-{4-[2-((2S,3S)-2-Amino-3-methyl-pentanoylamino)-1-triisopropylsilanyloxy-ethyl]-phenoxy}-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: 78 percent / NaH / dimethylformamide / 4 h / -30 °C

2.1: 73 percent / NaH₂PO₂ / Raney Ni / pyridine; acetic acid; H₂O / 3 h / 40 - 45 °C

3.1: 85 percent Turnov_. / Na / methanol / 0.5 h / 0 °C

4.1: 65 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 0 °C

5.1: 81 percent / HCO₂NH₄ / Pd/C / methanol / 2 h / 40 °C

6.1: 91 percent / DCC; NMM; HOBt / CH₂Cl₂ / 3 h / 0 - 20 °C

7.1: 87 percent / AcOH / tetrahydrofuran; H₂O / 3 h / 45 - 50 °C

8.1: NEt₃; TFAA; DMSO / CH₂Cl₂ / 3 h / -78 °C

8.2: 65 percent / KMnO₄ / aq. phosphate buffer; 2-methyl-propan-2-ol / 1 h / 20 °C / pH 4.12

9.1: 87 percent / MeOH / Pd/C / 1 h / 20 °C

With 4-methyl-morpholine; 2,6-dimethylpyridine; methanol; sodium hypophosphite; ammonium formate; sodium; sodium hydride; benzotriazol-1-ol; acetic acid; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic anhydride; palladium on activated charcoal; nickel; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; 3.1: Henry reaction / 8.1: Swern-Masamune oxidation;
DOI:10.1016/S0040-4039(03)00278-8

Reference yield:

: 123278-55-7
(4R,5S)-5-<(1,1-dimethylethyl)dimethylsilyl>oxymethyl-4-hydroxy-1-<(1,1-dimethylethoxy)carbonyl>-pyrrolidin-2-one

: 540508-57-4
(2S,3R)-3-{4-[2-((2S,3S)-2-Amino-3-methyl-pentanoylamino)-1-triisopropylsilanyloxy-ethyl]-phenoxy}-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: 88 percent / BH₃*SMe₂ / tetrahydrofuran / 5 h / Heating

2.1: 78 percent / NaH / dimethylformamide / 4 h / -30 °C

3.1: 73 percent / NaH₂PO₂ / Raney Ni / pyridine; acetic acid; H₂O / 3 h / 40 - 45 °C

4.1: 85 percent Turnov_. / Na / methanol / 0.5 h / 0 °C

5.1: 65 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 0 °C

6.1: 81 percent / HCO₂NH₄ / Pd/C / methanol / 2 h / 40 °C

7.1: 91 percent / DCC; NMM; HOBt / CH₂Cl₂ / 3 h / 0 - 20 °C

8.1: 87 percent / AcOH / tetrahydrofuran; H₂O / 3 h / 45 - 50 °C

9.1: NEt₃; TFAA; DMSO / CH₂Cl₂ / 3 h / -78 °C

9.2: 65 percent / KMnO₄ / aq. phosphate buffer; 2-methyl-propan-2-ol / 1 h / 20 °C / pH 4.12

10.1: 87 percent / MeOH / Pd/C / 1 h / 20 °C

With 4-methyl-morpholine; 2,6-dimethylpyridine; methanol; sodium hypophosphite; dimethylsulfide borane complex; ammonium formate; sodium; sodium hydride; benzotriazol-1-ol; acetic acid; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic anhydride; palladium on activated charcoal; nickel; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; 4.1: Henry reaction / 9.1: Swern-Masamune oxidation;
DOI:10.1016/S0040-4039(03)00278-8