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

Base Information

Chemical Name:(2R,3R)-3-{4-[2-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylamino)-1-triisopropylsilanyloxy-ethyl]-phenoxy}-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester
CAS No.:540508-52-9
Molecular Formula:C₄₁H₆₅N₃O₈Si
Molecular Weight:756.068
Hs Code.:

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

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

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

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

There total 8 articles about (2R,3R)-3-{4-[2-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylamino)-1-triisopropylsilanyloxy-ethyl]-phenoxy}-2-hydroxymethyl-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: 87.0%

: 540508-28-9
(2R,3R)-3-{4-[2-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylamino)-1-triisopropylsilanyloxy-ethyl]-phenoxy}-2-(tert-butyl-dimethyl-silanyloxymethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

: 540508-52-9
(2R,3R)-3-{4-[2-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylamino)-1-triisopropylsilanyloxy-ethyl]-phenoxy}-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: With acetic acid; In tetrahydrofuran; water; at 45 - 50 ℃; for 3h;
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

: 540508-52-9
(2R,3R)-3-{4-[2-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylamino)-1-triisopropylsilanyloxy-ethyl]-phenoxy}-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 78 percent / NaH / dimethylformamide / 4 h / -30 °C

2: 73 percent / NaH₂PO₂ / Raney Ni / pyridine; acetic acid; H₂O / 3 h / 40 - 45 °C

3: 85 percent Turnov_. / Na / methanol / 0.5 h / 0 °C

4: 65 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 0 °C

5: 81 percent / HCO₂NH₄ / Pd/C / methanol / 2 h / 40 °C

6: 91 percent / DCC; NMM; HOBt / CH₂Cl₂ / 3 h / 0 - 20 °C

7: 87 percent / AcOH / tetrahydrofuran; H₂O / 3 h / 45 - 50 °C

With 4-methyl-morpholine; 2,6-dimethylpyridine; sodium hypophosphite; ammonium formate; sodium; sodium hydride; benzotriazol-1-ol; acetic acid; dicyclohexyl-carbodiimide; palladium on activated charcoal; nickel; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; 3: Henry reaction;
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

: 540508-52-9
(2R,3R)-3-{4-[2-((2S,3S)-2-Benzyloxycarbonylamino-3-methyl-pentanoylamino)-1-triisopropylsilanyloxy-ethyl]-phenoxy}-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 88 percent / BH₃*SMe₂ / tetrahydrofuran / 5 h / Heating

2: 78 percent / NaH / dimethylformamide / 4 h / -30 °C

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

4: 85 percent Turnov_. / Na / methanol / 0.5 h / 0 °C

5: 65 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 0 °C

6: 81 percent / HCO₂NH₄ / Pd/C / methanol / 2 h / 40 °C

7: 91 percent / DCC; NMM; HOBt / CH₂Cl₂ / 3 h / 0 - 20 °C

8: 87 percent / AcOH / tetrahydrofuran; H₂O / 3 h / 45 - 50 °C

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