(S)-3-[(2S,3R,4R,5S)-2,3,4,6-tetrahydroxy-5-(L-leucyl)aminohexanoyl]amino-3-phenylpropionic acid

Base Information

• Chemical Name: (S)-3-[(2S,3R,4R,5S)-2,3,4,6-tetrahydroxy-5-(L-leucyl)aminohexanoyl]amino-3-phenylpropionic acid
• CAS No.: 219823-30-0
• Molecular Formula: C₂₁H₃₃N₃O₈
• Molecular Weight: 455.508
• Mol file: 219823-30-0.mol

Synonyms:(S)-3-[(2S,3R,4R,5S)-2,3,4,6-tetrahydroxy-5-(L-leucyl)aminohexanoyl]amino-3-phenylpropionic acid

Chemical Property of (S)-3-[(2S,3R,4R,5S)-2,3,4,6-tetrahydroxy-5-(L-leucyl)aminohexanoyl]amino-3-phenylpropionic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-[(2S,3R,4R,5S)-2,3,4,6-tetrahydroxy-5-(L-leucyl)aminohexanoyl]amino-3-phenylpropionic acid

There total 5 articles about (S)-3-[(2S,3R,4R,5S)-2,3,4,6-tetrahydroxy-5-(L-leucyl)aminohexanoyl]amino-3-phenylpropionic 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:

(S)-3-[(2S,3R,4R,5S)-5-((S)-2-Amino-4-methyl-pentanoylamino)-2,3,4,6-tetrahydroxy-hexanoylamino]-3-phenyl-propionic acid methyl ester (769905-82-0) → (S)-3-[(2S,3R,4R,5S)-2,3,4,6-tetrahydroxy-5-(L-leucyl)aminohexanoyl]amino-3-phenylpropionic acid (219823-30-0)

Guidance literature:

With sodium hydroxide; In water; at 20 ℃; for 1h;

DOI:10.7164/antibiotics.55.191

Reference yield:

N-tert-butoxycarbonyl-L-leucine (13139-15-6,53296-34-7) → (S)-3-[(2S,3R,4R,5S)-2,3,4,6-tetrahydroxy-5-(L-leucyl)aminohexanoyl]amino-3-phenylpropionic acid (219823-30-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 86 percent / 1-hydroxybenzotriazole; dicyclohexylcarbodiimide / dimethylformamide / 18 h / 20 °C

2: H₂ / 10 percent Pd/C / methanol; H₂O / 18 h / 10 °C / pH 2.0

3: NaBH₄ / methanol / 0.5 h / 20 °C

4: trifluoroacetic acid / 0.5 h / 20 °C

5: 1 N NaOH / H₂O / 1 h / 20 °C

With sodium hydroxide; sodium tetrahydroborate; hydrogen; benzotriazol-1-ol; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; water; N,N-dimethyl-formamide; trifluoroacetic acid;

DOI:10.7164/antibiotics.55.191

Reference yield:

(R)-3-{[(2S,3R,4R,5R,6S)-6-Benzyloxy-5-((S)-2-tert-butoxycarbonylamino-4-methyl-pentanoylamino)-3,4-dihydroxy-tetrahydro-pyran-2-carbonyl]-amino}-3-phenyl-propionic acid methyl ester → (S)-3-[(2S,3R,4R,5S)-2,3,4,6-tetrahydroxy-5-(L-leucyl)aminohexanoyl]amino-3-phenylpropionic acid (219823-30-0)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂ / 10 percent Pd/C / methanol; H₂O / 18 h / 10 °C / pH 2.0

2: NaBH₄ / methanol / 0.5 h / 20 °C

3: trifluoroacetic acid / 0.5 h / 20 °C

4: 1 N NaOH / H₂O / 1 h / 20 °C

With sodium hydroxide; sodium tetrahydroborate; hydrogen; palladium on activated charcoal; In methanol; water; trifluoroacetic acid;

DOI:10.7164/antibiotics.55.191

upstream raw materials:

(S)-3-[(2S,3R,4R,5S)-5-((S)-2-Amino-4-methyl-pentanoylamino)-2,3,4,6-tetrahydroxy-hexanoylamino]-3-phenyl-propionic acid methyl ester

N-tert-butoxycarbonyl-L-leucine

(S)-3-[(2S,3R,4R,5S)-5-((S)-2-tert-Butoxycarbonylamino-4-methyl-pentanoylamino)-2,3,4,6-tetrahydroxy-hexanoylamino]-3-phenyl-propionic acid methyl ester