(2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2R,3R,4R,5R)-3,5-dihydroxy-2,4-dimethyloctadecanoyl]amino]-3,3-dimethylpent-4-enoyl]amino]-3-hydroxybutanoyl]amino]-3-oxopropanoic acid

Base Information

• Chemical Name: (2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2R,3R,4R,5R)-3,5-dihydroxy-2,4-dimethyloctadecanoyl]amino]-3,3-dimethylpent-4-enoyl]amino]-3-hydroxybutanoyl]amino]-3-oxopropanoic acid
• CAS No.: 147334-89-2
• Molecular Formula: C₃₄H₆₁N₃O₉
• Molecular Weight: 655.873
• DSSTox Substance ID: DTXSID40163683
• Wikidata: Q83032668
• Mol file: 147334-89-2.mol

Synonyms:stevastelin B

Chemical Property of (2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2R,3R,4R,5R)-3,5-dihydroxy-2,4-dimethyloctadecanoyl]amino]-3,3-dimethylpent-4-enoyl]amino]-3-hydroxybutanoyl]amino]-3-oxopropanoic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 895.4°Cat760mmHg
• PKA: 12.15±0.70(Predicted)
• Flash Point: 495.3°C
• PSA: 212.83000
• Density: 1.111g/cm³
• LogP: 5.53330
• XLogP3: 6.1
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 26
• Exact Mass: 655.44078053
• Heavy Atom Count: 46
• Complexity: 958

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCC(C(C)C(C(C)C(=O)NC(C(=O)NC(C(C)O)C(=O)NC(C=O)C(=O)O)C(C)(C)C=C)O)O
• Isomeric SMILES: CCCCCCCCCCCCC[C@H]([C@@H](C)[C@H]([C@@H](C)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](C=O)C(=O)O)C(C)(C)C=C)O)O

Technology Process of (2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2R,3R,4R,5R)-3,5-dihydroxy-2,4-dimethyloctadecanoyl]amino]-3,3-dimethylpent-4-enoyl]amino]-3-hydroxybutanoyl]amino]-3-oxopropanoic acid

There total 31 articles about (2S)-2-[[(2S,3R)-2-[[(2S)-2-[[(2R,3R,4R,5R)-3,5-dihydroxy-2,4-dimethyloctadecanoyl]amino]-3,3-dimethylpent-4-enoyl]amino]-3-hydroxybutanoyl]amino]-3-oxopropanoic 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: 81.0%

acetic anhydride (108-24-7) + (3S,6S,9S,12R,13R,14R,15R)-13-Hydroxy-6-((R)-1-hydroxy-ethyl)-3-hydroxymethyl-9-isopropyl-12,14-dimethyl-15-tridecyl-1-oxa-4,7,10-triaza-cyclopentadecane-2,5,8,11-tetraone (350817-37-7) → Stevastelin B (147334-89-2)

Guidance literature:

With pyridine;

DOI:10.1055/s-2001-13382

Reference yield:

(3S,6S,9S,12R,13R,14R,15R)-3-Benzyloxymethyl-13-hydroxy-6-((R)-1-hydroxy-ethyl)-9-isopropyl-12,14-dimethyl-15-tridecyl-1-oxa-4,7,10-triaza-cyclopentadecane-2,5,8,11-tetraone (350817-30-0) → Stevastelin B (147334-89-2)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / Pd/C / methanol / 2 h / 25 °C

2: 8 mg / pyridine / 2 h / 0 °C

With pyridine; hydrogen; palladium on activated charcoal; In methanol;

DOI:10.1021/jo050625l

Reference yield:

(S)-3-Benzyloxy-2-[(2S,3R)-2-((S)-2-tert-butoxycarbonylamino-3-methyl-butyrylamino)-3-hydroxy-butyrylamino]-propionic acid (R)-1-((1R,2R,3R)-2-hydroxy-1,3-dimethyl-4-oxo-butyl)-tetradecyl ester (350817-36-6) → Stevastelin B (147334-89-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 2-methyl-2-butene; NaClO₂; NaH₂PO₄ / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 0.17 h / 25 °C

2: 100 percent / CH₂Cl₂ / 1 h / 0 °C

3: 47 percent / diethyl cyanophosphonate; triethylamine / dimethylformamide / 18 h / 25 °C

4: H₂ / Pd/C / methanol / 2 h / 25 °C

5: 8 mg / pyridine / 2 h / 0 °C

With pyridine; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; diethyl cyanophosphonate; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1021/jo050625l

upstream raw materials:

acetic anhydride

(3S,6S,9S,12R,13R,14R,15R)-13-Hydroxy-6-((R)-1-hydroxy-ethyl)-3-hydroxymethyl-9-isopropyl-12,14-dimethyl-15-tridecyl-1-oxa-4,7,10-triaza-cyclopentadecane-2,5,8,11-tetraone

tert-Butyl-dimethyl-{(R)-1-[(R)-1-((4S,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-ethyl]-tetradecyloxy}-silane

(S)-2-Amino-3-benzyloxy-propionic acid (R)-1-[(S)-1-((4S,5S)-2,2,5-trimethyl-[1,3]dioxan-4-yl)-ethyl]-tetradecyl ester

Downstream raw materials:

Benzoic acid (2S,3S,4S,5R)-3,5-dihydroxy-2,4-dimethyl-octadecyl ester