Aglafoline

Base Information

• Chemical Name: Aglafoline
• CAS No.: 143901-35-3
• Molecular Formula: C28H28 O8
• Molecular Weight: 492.526
• NSC Number: 695795
• DSSTox Substance ID: DTXSID50932140
• Nikkaji Number: J490.893G
• Wikidata: Q27133817
• Pharos Ligand ID: RPCZDD3BMRRQ
• Metabolomics Workbench ID: 63824
• ChEMBL ID: CHEMBL394528
• Mol file: 143901-35-3.mol

Synonyms:aglafoline

Chemical Property of Aglafoline

Chemical Property:

• Vapor Pressure: 2.23E-16mmHg at 25°C
• Melting Point: 92-93 °C(Solv: benzene (71-43-2); hexane (110-54-3))
• Boiling Point: 622.9°Cat760mmHg
• PKA: 11?+-.0.70(Predicted)
• Flash Point: 205.2°C
• PSA: 103.68000
• Density: 1.348g/cm³
• LogP: 3.13540
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 7
• Exact Mass: 492.17841785
• Heavy Atom Count: 36
• Complexity: 778

Purity/Quality:

97% ^*data from raw suppliers

Aglafoline 98+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)C23C(C(C(C2(C4=C(O3)C=C(C=C4OC)OC)O)O)C(=O)OC)C5=CC=CC=C5
• Isomeric SMILES: COC1=CC=C(C=C1)[C@]23[C@@H]([C@H]([C@H]([C@]2(C4=C(O3)C=C(C=C4OC)OC)O)O)C(=O)OC)C5=CC=CC=C5

Technology Process of Aglafoline

There total 41 articles about Aglafoline 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: 90.0%

(1R,2R,3S,3aR,8bS)-methyl 1,6,8b-trihydroxy-8-methoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-benzo[b]-cyclopenta[d]furan-2-carboxylate (960365-65-5) + diazomethyl-trimethyl-silane (18107-18-1) → aglafoline (143901-35-3)

Guidance literature:

In methanol; toluene; at 25 ℃; for 3h; Inert atmosphere;

DOI:10.1021/jm3011542

Reference yield: 80.0%

(2R,3S,3aR,8bR)-methyl 8b-hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-1-oxo-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta-[b]benzofuran-2-carboxylate → aglafoline (143901-35-3)

Guidance literature:

With acetic acid; tetramethylammonium triacetoxyborohydride; In acetonitrile; at 20 ℃;

DOI:10.1021/ja511728b

Reference yield: 76.0%

methyl 8b-hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-1-oxo-3-phenyl-2,3,3a,8a-tetrahydrocyclopentabenzofuran-2-carboxylate (136850-48-1) → methyl 1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8a-tetrahydrocyclopentabenzofuran-2(1H)-carboxylate (117828-50-9,143901-35-3,145679-25-0,145679-26-1,147059-47-0)

Guidance literature:

With sodium tetrahydroborate; In methanol; 1) 0 deg C, 3 h, 2) up to r. t., overnight;

upstream raw materials:

(±)-methyl (2R,3S,3aR,8bR)-8b-hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-1-oxo-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-2-carboxylate

(±)-(3S,3aR,8bR)-8b-hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydro-1H-cyclopenta[b]benzofuran-1-one

6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8b-tetrahydrocyclopentabenzofuran-1,8b(1H)-diol

methyl 8b-hydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-1-oxo-3-phenyl-2,3,3a,8a-tetrahydrocyclopentabenzofuran-2-carboxylate

Downstream raw materials:

rocaglamide

endo rocaglic acid

1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-N,N-dimethyl-3-phenyl-2,3,3a,8a-tetrahydrocyclopentabenzofuran-2(1H)-carboxamide

1,8b-dihydroxy-6,8-dimethoxy-3a-(4-methoxyphenyl)-3-phenyl-2,3,3a,8a-tetrahydrocyclopenta[b]benzofuran-2(1H)-carboxylic acid