Ambruticin

Base Information

• Chemical Name: Ambruticin
• CAS No.: 58857-02-6
• Molecular Formula: C28H42 O6
• Molecular Weight: 474.638
• UNII: X794618736
• DSSTox Substance ID: DTXSID701024202
• Nikkaji Number: J14.474F,J2.142.275D
• Wikidata: Q27293636
• NCI Thesaurus Code: C75987
• Metabolomics Workbench ID: 98876
• ChEMBL ID: CHEMBL522783
• Mol file: 58857-02-6.mol

Synonyms:ambruticin;ambruticin, sodium salt;W7783

Chemical Property of Ambruticin

Chemical Property:

• Vapor Pressure: 1.66E-17mmHg at 25°C
• Boiling Point: 611.5°C at 760 mmHg
• Flash Point: 194.8°C
• PSA: 96.22000
• Density: 1.201g/cm³
• LogP: 4.43110
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 474.29813906
• Heavy Atom Count: 34
• Complexity: 827

Purity/Quality:

99% ^*data from raw suppliers

AMBRUTICIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC1C(=CCC(O1)C(=CC(C)C=CC2C(C2C=CC3C(C(CC(O3)CC(=O)O)O)O)C)C)C
• Isomeric SMILES: CC[C@@H]1C(=CC[C@@H](O1)/C(=C/[C@H](C)/C=C/[C@H]2[C@H]([C@@H]2/C=C/[C@H]3[C@@H]([C@H](C[C@H](O3)CC(=O)O)O)O)C)/C)C
• Uses: Antifungal.
• Therapeutic Function: Antifungal

Technology Process of Ambruticin

There total 104 articles about Ambruticin 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: 95.0%

methyl 5β,6α-dihydroxypolyangioate (62711-77-7) → (+)-ambruticin S (58857-02-6)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; at 20 ℃; for 3.5h;

DOI:10.1016/S0040-4020(03)00370-3

Reference yield: 91.0%

(2S,3R,4S,6R)-2-((E)-2-((1S,2S,3R)-2-((R,1E,4E)-5-((2R,6R)-6-ethyl-5-methyl-3,6-dihydro-2H-pyran-2-yl)-3-methylhexa-1,4-dien-1-yl)-3-methylcyclopropyl)vinyl)-6-(2-hydroxyethyl)tetrahydro-2H-pyran-3,4-diol (63511-77-3) → (+)-ambruticin S (58857-02-6)

Guidance literature:

With oxygen; sodium hydrogencarbonate; platinum; In water; isopropyl alcohol; acetone; at 50 ℃;

DOI:10.1021/jo100956v

Reference yield: 89.0%

methyl 5β,6α-dibenzyloxypolyangioate (130799-17-6) → (+)-ambruticin S (58857-02-6)

Guidance literature:

methyl 5β,6α-dibenzyloxypolyangioate; With lithium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 8h;

With lithium; In ethanol; ammonia; at -78 ℃; for 0.166667h;

DOI:10.1002/1521-3773(20020104)41:1<176::AID-ANIE176>3.0.CO;2-#

upstream raw materials:

5β,6α-dibenzyloxypolyangioic acid

methyl 5β,6α-dibenzyloxypolyangioate

methyl 5β,6α-dihydroxypolyangioate

(2S,3R,4S,6R)-2-((E)-2-((1S,2S,3R)-2-((R,1E,4E)-5-((2R,6R)-6-ethyl-5-methyl-3,6-dihydro-2H-pyran-2-yl)-3-methylhexa-1,4-dien-1-yl)-3-methylcyclopropyl)vinyl)-6-(2-hydroxyethyl)tetrahydro-2H-pyran-3,4-diol

Downstream raw materials:

methyl 5β,6α-di-tert-butyldimethylsilyloxypolyangioate

methyl [(2S,4S,5R,6S)-4,5-bis(tert-butyldimethylsilyloxy)-6-hydroxymethyltetrahydro-2H-pyran-2-yl] acetate

(1S,2S)-3-methylcyclopropane-1,2-dicarboxylic acid

methyl 5β,6α-dihydroxypolyangioate

Refernces

• 1、 Berberich, Stephen M.,Cherney, Robert J.,Colucci, John,Courillon, Christine,Geraci, Leo S.,Kirkland, Thomas A.,Marx, Matthew A.,Schneider, Matthias F.,Martin, Stephen F.. "Total synthesis of (+)-ambruticin S". . p. 6819 - 6832. Retrieved 2007/10/03.
• 2、 Kirkland,Colucci,Geraci,Marx,Schneider,Kaelin D.E.,Martin. "Total synthesis of (+)-ambruticin S". . p. 12432 - 12433. Retrieved 2007/10/03.