(S)-2-{(R)-2-[3-(tert-Butoxycarbonyl-methyl-amino)-propionyloxy]-4-methyl-pentanoylamino}-4-methyl-pentanoic acid (S)-1-[((S)-1-benzyloxycarbonyl-2-phenyl-ethyl)-methyl-carbamoyl]-3-methyl-butyl ester

Base Information

• Chemical Name: (S)-2-{(R)-2-[3-(tert-Butoxycarbonyl-methyl-amino)-propionyloxy]-4-methyl-pentanoylamino}-4-methyl-pentanoic acid (S)-1-[((S)-1-benzyloxycarbonyl-2-phenyl-ethyl)-methyl-carbamoyl]-3-methyl-butyl ester
• CAS No.: 223270-83-5
• Molecular Formula: C₄₄H₆₅N₃O₁₀
• Molecular Weight: 796.014

Synonyms:(S)-2-{(R)-2-[3-(tert-Butoxycarbonyl-methyl-amino)-propionyloxy]-4-methyl-pentanoylamino}-4-methyl-pentanoic acid (S)-1-[((S)-1-benzyloxycarbonyl-2-phenyl-ethyl)-methyl-carbamoyl]-3-methyl-butyl ester

Chemical Property of (S)-2-{(R)-2-[3-(tert-Butoxycarbonyl-methyl-amino)-propionyloxy]-4-methyl-pentanoylamino}-4-methyl-pentanoic acid (S)-1-[((S)-1-benzyloxycarbonyl-2-phenyl-ethyl)-methyl-carbamoyl]-3-methyl-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (S)-2-{(R)-2-[3-(tert-Butoxycarbonyl-methyl-amino)-propionyloxy]-4-methyl-pentanoylamino}-4-methyl-pentanoic acid (S)-1-[((S)-1-benzyloxycarbonyl-2-phenyl-ethyl)-methyl-carbamoyl]-3-methyl-butyl ester

There total 11 articles about (S)-2-{(R)-2-[3-(tert-Butoxycarbonyl-methyl-amino)-propionyloxy]-4-methyl-pentanoylamino}-4-methyl-pentanoic acid (S)-1-[((S)-1-benzyloxycarbonyl-2-phenyl-ethyl)-methyl-carbamoyl]-3-methyl-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:

(R)-2-hydroxy-4-methylpentanoic acid (20312-37-2,498-36-2) → (S)-2-{(R)-2-[3-(tert-Butoxycarbonyl-methyl-amino)-propionyloxy]-4-methyl-pentanoylamino}-4-methyl-pentanoic acid (S)-1-[((S)-1-benzyloxycarbonyl-2-phenyl-ethyl)-methyl-carbamoyl]-3-methyl-butyl ester (223270-83-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 70 percent / PhI(OAc)2, I₂ / -10 °C

2: EDCI, DMAP, TEA

3: H₂ / 10 percent Pd/C / methanol; ethyl acetate

4: BOP-Cl, DIEA / 0 °C

With dmap; [bis(acetoxy)iodo]benzene; TEA; hydrogen; iodine; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In methanol; ethyl acetate;

DOI:10.1016/S0960-894X(99)00038-4

Reference yield:

(R)-leucine (328-38-1,21675-61-6,25248-98-0,70-45-1) → (S)-2-{(R)-2-[3-(tert-Butoxycarbonyl-methyl-amino)-propionyloxy]-4-methyl-pentanoylamino}-4-methyl-pentanoic acid (S)-1-[((S)-1-benzyloxycarbonyl-2-phenyl-ethyl)-methyl-carbamoyl]-3-methyl-butyl ester (223270-83-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 51 percent / NaNO₂, H₂SO₄ / H₂O

2: 70 percent / PhI(OAc)2, I₂ / -10 °C

3: EDCI, DMAP, TEA

4: H₂ / 10 percent Pd/C / methanol; ethyl acetate

5: BOP-Cl, DIEA / 0 °C

With dmap; [bis(acetoxy)iodo]benzene; TEA; sulfuric acid; hydrogen; iodine; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; sodium nitrite; palladium on activated charcoal; In methanol; water; ethyl acetate;

DOI:10.1016/S0960-894X(99)00038-4

Reference yield:

(S)-2-hydroxyl-3,3-dimethylbutyric acid (13748-90-8,498-36-2) → (S)-2-{(R)-2-[3-(tert-Butoxycarbonyl-methyl-amino)-propionyloxy]-4-methyl-pentanoylamino}-4-methyl-pentanoic acid (S)-1-[((S)-1-benzyloxycarbonyl-2-phenyl-ethyl)-methyl-carbamoyl]-3-methyl-butyl ester (223270-83-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 70 percent / PhI(OAc)2, I₂ / -10 °C

2: EDCI, DMAP, TEA

3: H₂ / 10 percent Pd/C / methanol; ethyl acetate

4: 84 percent / BOP-Cl, NMM

5: 95 percent / TFA / -10 °C

6: BOP-Cl, DIEA / 0 °C

With 4-methyl-morpholine; dmap; [bis(acetoxy)iodo]benzene; TEA; hydrogen; iodine; bis-(2-oxo-3-oxazolidinyl)phosphoryl chloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium on activated charcoal; In methanol; ethyl acetate;

DOI:10.1016/S0960-894X(99)00038-4

upstream raw materials:

H-L-Leu-O-L-Leu-N(Me)-L-Phe phenylmethyl ester

2-[3-(tert-butoxycarbonyl-methyl-amino)-propionyloxy]-4-methyl-pentanoic acid

(R)-leucine

L-leucine

Downstream raw materials:

(S)-4-Methyl-2-[(R)-4-methyl-2-(3-methylamino-propionyloxy)-pentanoylamino]-pentanoic acid (S)-1-[((S)-1-carboxy-2-phenyl-ethyl)-methyl-carbamoyl]-3-methyl-butyl ester

(S)-4-Methyl-2-[(R)-4-methyl-2-(3-methylamino-propionyloxy)-pentanoylamino]-pentanoic acid (S)-1-[((S)-1-benzyloxycarbonyl-2-phenyl-ethyl)-methyl-carbamoyl]-3-methyl-butyl ester

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