Plagiogyrin A

Base Information

• Chemical Name: Plagiogyrin A
• CAS No.: 91486-94-1
• Molecular Formula: C15H14O7
• Molecular Weight: 306.2675
• Wikidata: Q105215950
• Mol file: 91486-94-1.mol

Synonyms:Plagiogyrin A;91486-94-1;NSC605337;4,8-Epoxyfuro(2,3-d)oxepin-2(3H)-one,hexahydro-4,5-dihydroxy-3-((4-hydroxyphenyl)methylene)-, (3E,3aR,4R,5S,8R,8aS)-

Chemical Property of Plagiogyrin A

Chemical Property:

• Vapor Pressure: 8.09E-17mmHg at 25°C
• Boiling Point: 631.5°Cat760mmHg
• Flash Point: 243.4°C
• Density: 1.685g/cm³
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 1
• Exact Mass: 306.07395278
• Heavy Atom Count: 22
• Complexity: 510

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2C3C(C(=CC4=CC=C(C=C4)O)C(=O)O3)C(O2)(C(O1)O)O
• Isomeric SMILES: C1[C@@H]2[C@@H]3[C@@H](/C(=C\C4=CC=C(C=C4)O)/C(=O)O3)[C@@](O2)([C@H](O1)O)O

Technology Process of Plagiogyrin A

There total 6 articles about Plagiogyrin A 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: 49.0%

(4R,5S)-3-((E)-4-((tert-butyldimethylsilyl)oxy)benzylidene)-4-(2-diazoacetyl)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)dihydrofuran-2(3H)-one + 3,3-dimethyldioxirane (74087-85-7) → (3aR,4R,5S,8R,8aS)-4,5-dihydroxy-3-((E)-4-hydroxybenzylidene)hexahydro-4,8-epoxyfuro[2,3-d]oxepin-2(3H)-one (91486-94-1)

Guidance literature:

(4R,5S)-3-((E)-4-((tert-butyldimethylsilyl)oxy)benzylidene)-4-(2-diazoacetyl)-5-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)dihydrofuran-2(3H)-one; 3,3-dimethyldioxirane; In acetone; at 20 ℃; for 0.166667h; Inert atmosphere;

With TAS-F; In N,N-dimethyl-formamide; acetonitrile; at 0 ℃; for 0.166667h;

DOI:10.1021/acs.orglett.6b02629

Reference yield:

(E)-4-(allyloxy)-2-(4-(allyloxy)benzylidene)-4-oxobutanoic acid → (3aR,4R,5S,8R,8aS)-4,5-dihydroxy-3-((E)-4-hydroxybenzylidene)hexahydro-4,8-epoxyfuro[2,3-d]oxepin-2(3H)-one (91486-94-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

1.2: 0.5 h / 20 °C / Inert atmosphere

2.1: sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

3.1: 1H-imidazole / water; N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere

3.2: 1 h / 20 °C / Inert atmosphere

3.3: 3 h / 0 °C / Inert atmosphere

4.1: acetone / 0.17 h / 20 °C / Inert atmosphere

4.2: 0.17 h / 0 °C

With 1H-imidazole; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; lithium hexamethyldisilazane; In tetrahydrofuran; water; N,N-dimethyl-formamide; acetone;

DOI:10.1021/acs.orglett.6b02629

Reference yield:

allyl (2S,3R)-4-((E)-4-(allyloxy)benzylidene)-2-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-5-oxotetrahydrofuran-3-carboxylate → (3aR,4R,5S,8R,8aS)-4,5-dihydroxy-3-((E)-4-hydroxybenzylidene)hexahydro-4,8-epoxyfuro[2,3-d]oxepin-2(3H)-one (91486-94-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

2.1: 1H-imidazole / water; N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere

2.2: 1 h / 20 °C / Inert atmosphere

2.3: 3 h / 0 °C / Inert atmosphere

3.1: acetone / 0.17 h / 20 °C / Inert atmosphere

3.2: 0.17 h / 0 °C

With 1H-imidazole; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; water; N,N-dimethyl-formamide; acetone;

DOI:10.1021/acs.orglett.6b02629

upstream raw materials:

3,3-dimethyldioxirane

4-(2-propenyloxy)benzaldehyde

Acetic acid (7R,7aS)-5-acetoxy-7-acetoxymethyl-3-[1-(4-acetoxy-phenyl)-meth-(Z)-ylidene]-2-oxo-3,5,7,7a-tetrahydro-2H-furo[2,3-c]pyran-4-yl ester

Downstream raw materials:

Acetic acid 2-acetoxy-1-{(2S,3S)-4-[1-(4-acetoxy-phenyl)-meth-(Z)-ylidene]-5-oxo-3-quinoxalin-2-yl-tetrahydro-furan-2-yl}-ethyl ester

Acetic acid 2-{(2S,3S)-4-[1-(4-acetoxy-phenyl)-meth-(Z)-ylidene]-5-oxo-3-quinoxalin-2-yl-tetrahydro-furan-2-yl}-2-hydroxy-ethyl ester

Acetic acid (3aR,6R,6aS)-3-[1-(4-acetoxy-phenyl)-meth-(E)-ylidene]-2,4-dioxo-hexahydro-furo[3,4-b]furan-6-ylmethyl ester

(4S,5S)-5-(1,2-Dihydroxy-ethyl)-3-[1-(4-hydroxy-phenyl)-meth-(Z)-ylidene]-4-quinoxalin-2-yl-dihydro-furan-2-one