Griseucin A

Base Information

• Chemical Name: Griseucin A
• CAS No.: 59554-11-9
• Molecular Formula: C22H20O10
• Molecular Weight: 444.3882
• DSSTox Substance ID: DTXSID30974962
• Mol file: 59554-11-9.mol

Synonyms:Griseucin A;BRN 4728584;59554-11-9;Spiro(5H-furo(3,2-b)naphtho(2,3-d)pyran-5,2'-(2H)-pyran)-2,6,11-(3H)-trione, 4'-(acetyloxy)-3',3a,4',5',6',11b-hexahydro-3',7-dihydroxy-6'-methyl-, (2'S-(2'-alpha(3ar*,11bR*),3'-alpha,4'-alpha,6'-beta))-;DTXSID30974962;LS-146129;3',7-Dihydroxy-6'-methyl-2,6,11-trioxo-2,3,3a,6,11,11b-hexahydrospiro[furo[3,2-b]naphtho[2,3-d]pyran-5,2'-oxan]-4'-yl acetate

Chemical Property of Griseucin A

Chemical Property:

• Boiling Point: 748.2°Cat760mmHg
• Flash Point: 265.4°C
• PSA: 145.66000
• Density: 1.59g/cm³
• LogP: 0.57980
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 2
• Exact Mass: 444.10564683
• Heavy Atom Count: 32
• Complexity: 924

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC(C(C2(O1)C3=C(C4C(O2)CC(=O)O4)C(=O)C5=C(C3=O)C(=CC=C5)O)O)OC(=O)C

Technology Process of Griseucin A

There total 17 articles about Griseucin 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: 100.0%

4’-deacetyl griseusin + acetyl chloride (75-36-5) → griseusin A (59554-11-9)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃;

Reference yield: 81.0%

(2R,3R,4R,5'R,6R,9'R)-3-hydroxy-11'-methoxy-6,18',18'-trimethyl-7'-oxo-4',8',17',19'-tetraoxaspiro[oxane-2,3'-pentacyclo[10.7.1.O2,10.O5,9.O16,20]icosane]-1'(20'),2'(10'),11',13',15'-pentaen-4-yl acetate → griseusin A (59554-11-9)

Guidance literature:

With silver(II) oxide; nitric acid; In tetrahydrofuran; at 0 ℃; for 0.166667h;

DOI:10.1002/anie.201505022

Reference yield:

(4R,5R)-4-hydroxy-5-(6-methoxy-2,2-dimethylnaphtho[1,8-de][1,3]dioxin-5-yl)dihydrofuran-2(3H)-one → griseusin A (59554-11-9)

Guidance literature:

Multi-step reaction with 6 steps

1: palladium diacetate; lithium carbonate; silver carbonate; 1,3-bis-(diphenylphosphino)propane / 1,2-dichloro-ethane / 16 h / 80 °C

2: pyridine; pyridine hydrogenfluoride / dichloromethane / 8 h / 20 °C

3: trifluorormethanesulfonic acid; 3,3-dimethyldioxirane / acetone; dichloromethane / 4 h / -78 - 0 °C

4: lithium borohydride / tetrahydrofuran / 1 h / -78 °C

5: N-Methyldicyclohexylamine / dichloromethane / 40 h / 20 °C

6: silver(II) oxide; nitric acid / tetrahydrofuran / 0.17 h / 0 °C

With pyridine; silver(II) oxide; lithium borohydride; trifluorormethanesulfonic acid; N-Methyldicyclohexylamine; 1,3-bis-(diphenylphosphino)propane; nitric acid; palladium diacetate; 3,3-dimethyldioxirane; lithium carbonate; pyridine hydrogenfluoride; silver carbonate; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; acetone;

DOI:10.1002/anie.201505022

upstream raw materials:

acetyl chloride

(R)-5-((tert-butyldimethylsilyl)oxy)hex-1-en-3-one

1,5-dihydroxynaphthalene