Bengamide B

Base Information

• Chemical Name: Bengamide B
• CAS No.: 104947-69-5
• Molecular Formula: C₃₂H₅₈N₂O₈
• Molecular Weight: 598.821
• Nikkaji Number: J274.275F
• Wikidata: Q104403521
• Metabolomics Workbench ID: 134358
• ChEMBL ID: CHEMBL446079
• Mol file: 104947-69-5.mol

Synonyms:bengamide B

Chemical Property of Bengamide B

Chemical Property:

• Vapor Pressure: 1.16E-27mmHg at 25°C
• Boiling Point: 774°Cat760mmHg
• Flash Point: 421.9°C
• PSA: 149.12000
• Density: 1.11g/cm³
• LogP: 4.42440
• XLogP3: 6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 22
• Exact Mass: 598.41931681
• Heavy Atom Count: 42
• Complexity: 805

Purity/Quality:

≥97% by HPLC ^*data from raw suppliers

BengamideB ≥97%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCCCCC(=O)OC1CCC(C(=O)N(C1)C)NC(=O)C(C(C(C(C=CC(C)C)O)O)O)OC
• Isomeric SMILES: CCCCCCCCCCCCCC(=O)O[C@H]1CC[C@@H](C(=O)N(C1)C)NC(=O)[C@@H]([C@@H]([C@H]([C@@H](/C=C/C(C)C)O)O)O)OC

Technology Process of Bengamide B

There total 58 articles about Bengamide B 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: 89.0%

(3S,6S)-6-[((2R,3R,4R,5R,6E)-5-{[(tert-butyl)dimethylsilyl]oxy}-3-hydroxy-2-methoxy-8-methyl-4-[(2-naphthyl)methoxy]non-6-enoyl)amino]-2,3,4,5,6,7-hexahydro-7-oxo-1-methylazepin-3-yl tetradecanoate (442913-40-8) → bengamide B (104947-69-5)

Guidance literature:

(3S,6S)-6-[((2R,3R,4R,5R,6E)-5-{[(tert-butyl)dimethylsilyl]oxy}-3-hydroxy-2-methoxy-8-methyl-4-[(2-naphthyl)methoxy]non-6-enoyl)amino]-2,3,4,5,6,7-hexahydro-7-oxo-1-methylazepin-3-yl tetradecanoate; With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; dichloromethane; at 20 ℃; for 2h;

With pyridinium p-toluenesulfonate; In methanol; dichloromethane; at 45 ℃; for 6h;

DOI:10.1002/hlca.200290026

Reference yield: 73.0%

Tetradecanoic acid (3S,6S)-6-{(R)-2-[(4R,5S,6R)-5-hydroxy-2,2-dimethyl-6-((E)-3-methyl-but-1-enyl)-[1,3]dioxan-4-yl]-2-methoxy-acetylamino}-1-methyl-7-oxo-azepan-3-yl ester (1054610-81-9) → bengamide B (104947-69-5)

Guidance literature:

With trifluoroacetic acid; In tetrahydrofuran; water; at 0 ℃; for 0.333333h;

DOI:10.1021/jo0017133

Reference yield: 54.0%

Tetradecanoic acid (3S,6S)-1-methyl-7-oxo-6-[(E)-(2R,3S,4S,5R)-3,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-8-methyl-non-6-enoylamino]-azepan-3-yl ester (137789-58-3) → bengamide B (104947-69-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1.5h;

DOI:10.1016/S0040-4039(00)79423-8

upstream raw materials:

Tetradecanoic acid (3S,6S)-1-methyl-7-oxo-6-[(E)-(2R,3S,4S,5R)-3,4,5-tris-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-8-methyl-non-6-enoylamino]-azepan-3-yl ester

Tetradecanoic acid (3S,6S)-6-{(R)-2-[(4R,5S,6R)-5-hydroxy-2,2-dimethyl-6-((E)-3-methyl-but-1-enyl)-[1,3]dioxan-4-yl]-2-methoxy-acetylamino}-1-methyl-7-oxo-azepan-3-yl ester

(3S,6S)-6-[((2R,3R,4R,5R,6E)-5-{[(tert-butyl)dimethylsilyl]oxy}-3-hydroxy-2-methoxy-8-methyl-4-[(2-naphthyl)methoxy]non-6-enoyl)amino]-2,3,4,5,6,7-hexahydro-7-oxo-1-methylazepin-3-yl tetradecanoate

(E)-4-methylpent-2-enal