(3S,4R)-4-Benzyloxycarbonylamino-5-methyl-3-triisopropylsilanyloxy-hexanoic acid (S)-2-methyl-1-pentafluorophenyloxycarbonyl-propyl ester

Base Information

Chemical Name:(3S,4R)-4-Benzyloxycarbonylamino-5-methyl-3-triisopropylsilanyloxy-hexanoic acid (S)-2-methyl-1-pentafluorophenyloxycarbonyl-propyl ester
CAS No.:325687-69-2
Molecular Formula:C₃₅H₄₈F₅NO₇Si
Molecular Weight:717.846
Hs Code.:

(3S,4R)-4-Benzyloxycarbonylamino-5-methyl-3-triisopropylsilanyloxy-hexanoic acid (S)-2-methyl-1-pentafluorophenyloxycarbonyl-propyl ester

Synonyms:(3S,4R)-4-Benzyloxycarbonylamino-5-methyl-3-triisopropylsilanyloxy-hexanoic acid (S)-2-methyl-1-pentafluorophenyloxycarbonyl-propyl ester

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Chemical Property of (3S,4R)-4-Benzyloxycarbonylamino-5-methyl-3-triisopropylsilanyloxy-hexanoic acid (S)-2-methyl-1-pentafluorophenyloxycarbonyl-propyl ester

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Technology Process of (3S,4R)-4-Benzyloxycarbonylamino-5-methyl-3-triisopropylsilanyloxy-hexanoic acid (S)-2-methyl-1-pentafluorophenyloxycarbonyl-propyl ester

There total 14 articles about (3S,4R)-4-Benzyloxycarbonylamino-5-methyl-3-triisopropylsilanyloxy-hexanoic acid (S)-2-methyl-1-pentafluorophenyloxycarbonyl-propyl 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:

: 17407-55-5
(S)-2-Hydroxy-3-methylbutanoic acid

: 325687-69-2
(3S,4R)-4-Benzyloxycarbonylamino-5-methyl-3-triisopropylsilanyloxy-hexanoic acid (S)-2-methyl-1-pentafluorophenyloxycarbonyl-propyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 96 percent / K₂CO₃ / Bu₄NI / dimethylformamide / 1 h / 20 °C

2: 60 percent / EDAC*HCl; DMAP / CH₂Cl₂ / 0 - 20 °C

3: 100 percent / Pd(PPh₃)4; morpholine / tetrahydrofuran / 20 °C

4: Pyr / CH₂Cl₂

With morpholine; pyridine; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja010222c

Reference yield:

: 72-18-4,25609-85-2,7004-03-7,921-10-8
L-valine

: 325687-69-2
(3S,4R)-4-Benzyloxycarbonylamino-5-methyl-3-triisopropylsilanyloxy-hexanoic acid (S)-2-methyl-1-pentafluorophenyloxycarbonyl-propyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 78 percent / 1N aq. H₂SO₄; NaNO₂ / 0 - 20 °C

2: 96 percent / K₂CO₃ / Bu₄NI / dimethylformamide / 1 h / 20 °C

3: 60 percent / EDAC*HCl; DMAP / CH₂Cl₂ / 0 - 20 °C

4: 100 percent / Pd(PPh₃)4; morpholine / tetrahydrofuran / 20 °C

5: Pyr / CH₂Cl₂

With morpholine; pyridine; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sulfuric acid; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium nitrite; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja010222c

Reference yield:

: 1685-33-2
N-[(benzyloxy)carbonyl]-D-valine

: 325687-69-2
(3S,4R)-4-Benzyloxycarbonylamino-5-methyl-3-triisopropylsilanyloxy-hexanoic acid (S)-2-methyl-1-pentafluorophenyloxycarbonyl-propyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 95 percent / EDAC*HCl; DMAP / CH₂Cl₂ / 0 - 20 °C

2: 83 percent / tetrahydrofuran / -78 °C

3: 77 percent / potassium borohydride / methanol / -30 - 0 °C

4: 82 percent / 2,6-lutidine / CH₂Cl₂ / 20 °C

5: 81 percent / aq. NaOH / tetrahydrofuran; methanol / 0 - 20 °C

6: 60 percent / EDAC*HCl; DMAP / CH₂Cl₂ / 0 - 20 °C

7: 100 percent / Pd(PPh₃)4; morpholine / tetrahydrofuran / 20 °C

8: Pyr / CH₂Cl₂

With morpholine; pyridine; 2,6-dimethylpyridine; dmap; sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium borohydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1021/ja010222c