Griseucin B

Base Information

• Chemical Name: Griseucin B
• CAS No.: 59554-12-0
• Molecular Formula: C22H22O10
• Molecular Weight: 446.4
• DSSTox Substance ID: DTXSID90974963
• Mol file: 59554-12-0.mol

Synonyms:Griseucin B;BRN 4729197;59554-12-0;Spiro(1H-naphtho(2,3-C)pyran-1,2'-(2H)-pyran)-3-acetic acid, 4'-(acetyloxy)-3,3',4,4',5,5',6'10-octahydro-3',9-dihydroxy-6'-methyl-5,10-dioxo-, (2'S-(2'-alpha-(S*),3'-alpha,4'-alpha,6'-beta))-;DTXSID90974963;LS-146300;[4'-(Acetyloxy)-3',9-dihydroxy-6'-methyl-5,10-dioxo-3,4,5,10-tetrahydrospiro[naphtho[2,3-c]pyran-1,2'-oxan]-3-yl]acetic acid

Chemical Property of Griseucin B

Chemical Property:

• XLogP3: 0.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 4
• Exact Mass: 446.12129689
• Heavy Atom Count: 32
• Complexity: 878

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1CC(C(C2(O1)C3=C(CC(O2)CC(=O)O)C(=O)C4=C(C3=O)C(=CC=C4)O)O)OC(=O)C

Technology Process of Griseucin B

There total 12 articles about Griseucin 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:

5-bromo-6-methoxy-2,2-dimethylnaphtho[1,8-de][1,3]dioxine → griseusin B (59554-12-0)

Guidance literature:

Multi-step reaction with 12 steps

1.1: Triisopropyl borate; n-butyllithium / tetrahydrofuran / 2 h / -78 °C

2.1: palladium diacetate; potassium fluoride / 1,4-dioxane / 2 h / 20 °C

3.1: copper(l) chloride; S-R_p-Josiphos; sodium t-butanolate; bis(pinacol)diborane / tetrahydrofuran / 16 h / 0 - 20 °C

3.2: 2 h / 20 °C

4.1: palladium diacetate; lithium carbonate; silver carbonate / chloroform / 16 h / 80 °C

5.1: triethylamine; pyridine hydrogenfluoride / 1,4-dioxane / 1 h / 20 °C

6.1: 3,3-dimethyldioxirane; trifluorormethanesulfonic acid / dichloromethane / 2 h / -78 - -20 °C

7.1: silver(l) oxide / 1-methyl-pyrrolidin-2-one / 36 h / 20 °C

8.1: lithium borohydride / tetrahydrofuran / 0.5 h / -78 °C

9.1: lithium hydroxide / methanol / 1 h / 20 °C

10.1: 1,4-diaza-bicyclo[2.2.2]octane / dichloromethane / 40 h / 20 °C

11.1: palladium on activated charcoal; hydrogen / methanol / 4 h / 20 °C

12.1: silver(II) oxide; nitric acid / 0.5 h / -10 °C

With 1,4-diaza-bicyclo[2.2.2]octane; silver(II) oxide; potassium fluoride; lithium borohydride; n-butyllithium; Triisopropyl borate; trifluorormethanesulfonic acid; palladium on activated charcoal; S-R_p-Josiphos; hydrogen; nitric acid; palladium diacetate; 3,3-dimethyldioxirane; lithium carbonate; pyridine hydrogenfluoride; triethylamine; silver carbonate; bis(pinacol)diborane; copper(l) chloride; silver(l) oxide; lithium hydroxide; sodium t-butanolate; In tetrahydrofuran; 1,4-dioxane; 1-methyl-pyrrolidin-2-one; methanol; dichloromethane; chloroform; 2.1: |Suzuki Coupling;

DOI:10.1039/c9sc02289a

Reference yield:

C14H15BO5 → griseusin B (59554-12-0)

Guidance literature:

Multi-step reaction with 11 steps

1.1: palladium diacetate; potassium fluoride / 1,4-dioxane / 2 h / 20 °C

2.1: copper(l) chloride; S-R_p-Josiphos; sodium t-butanolate; bis(pinacol)diborane / tetrahydrofuran / 16 h / 0 - 20 °C

2.2: 2 h / 20 °C

3.1: palladium diacetate; lithium carbonate; silver carbonate / chloroform / 16 h / 80 °C

4.1: triethylamine; pyridine hydrogenfluoride / 1,4-dioxane / 1 h / 20 °C

5.1: 3,3-dimethyldioxirane; trifluorormethanesulfonic acid / dichloromethane / 2 h / -78 - -20 °C

6.1: silver(l) oxide / 1-methyl-pyrrolidin-2-one / 36 h / 20 °C

7.1: lithium borohydride / tetrahydrofuran / 0.5 h / -78 °C

8.1: lithium hydroxide / methanol / 1 h / 20 °C

9.1: 1,4-diaza-bicyclo[2.2.2]octane / dichloromethane / 40 h / 20 °C

10.1: palladium on activated charcoal; hydrogen / methanol / 4 h / 20 °C

11.1: silver(II) oxide; nitric acid / 0.5 h / -10 °C

With 1,4-diaza-bicyclo[2.2.2]octane; silver(II) oxide; potassium fluoride; lithium borohydride; trifluorormethanesulfonic acid; palladium on activated charcoal; S-R_p-Josiphos; hydrogen; nitric acid; palladium diacetate; 3,3-dimethyldioxirane; lithium carbonate; pyridine hydrogenfluoride; triethylamine; silver carbonate; bis(pinacol)diborane; copper(l) chloride; silver(l) oxide; lithium hydroxide; sodium t-butanolate; In tetrahydrofuran; 1,4-dioxane; 1-methyl-pyrrolidin-2-one; methanol; dichloromethane; chloroform; 1.1: |Suzuki Coupling;

DOI:10.1039/c9sc02289a

Reference yield:

C19H20O5 → griseusin B (59554-12-0)

Guidance literature:

Multi-step reaction with 10 steps

1.1: copper(l) chloride; S-R_p-Josiphos; sodium t-butanolate; bis(pinacol)diborane / tetrahydrofuran / 16 h / 0 - 20 °C

1.2: 2 h / 20 °C

2.1: palladium diacetate; lithium carbonate; silver carbonate / chloroform / 16 h / 80 °C

3.1: triethylamine; pyridine hydrogenfluoride / 1,4-dioxane / 1 h / 20 °C

4.1: 3,3-dimethyldioxirane; trifluorormethanesulfonic acid / dichloromethane / 2 h / -78 - -20 °C

5.1: silver(l) oxide / 1-methyl-pyrrolidin-2-one / 36 h / 20 °C

6.1: lithium borohydride / tetrahydrofuran / 0.5 h / -78 °C

7.1: lithium hydroxide / methanol / 1 h / 20 °C

8.1: 1,4-diaza-bicyclo[2.2.2]octane / dichloromethane / 40 h / 20 °C

9.1: palladium on activated charcoal; hydrogen / methanol / 4 h / 20 °C

10.1: silver(II) oxide; nitric acid / 0.5 h / -10 °C

With 1,4-diaza-bicyclo[2.2.2]octane; silver(II) oxide; lithium borohydride; trifluorormethanesulfonic acid; palladium on activated charcoal; S-R_p-Josiphos; hydrogen; nitric acid; palladium diacetate; 3,3-dimethyldioxirane; lithium carbonate; pyridine hydrogenfluoride; triethylamine; silver carbonate; bis(pinacol)diborane; copper(l) chloride; silver(l) oxide; lithium hydroxide; sodium t-butanolate; In tetrahydrofuran; 1,4-dioxane; 1-methyl-pyrrolidin-2-one; methanol; dichloromethane; chloroform;

DOI:10.1039/c9sc02289a

upstream raw materials:

(S)-3-Hydroxy-4-(6-methoxy-2,2-dimethyl-naphtho[1,8-de][1,3]dioxin-5-yl)-butyric acid methyl ester

Refernces