5,11-Methanofuro(3,4-d)(3)benzoxonin-1,12(3H,5H)-dione, 6,6a,7,8,9,10,10a,11-octahydro-6,6a-dihydroxy-11,13-dimethyl-3-methylene-, (5R-(5R,6S,6aR,10aR,11S,13R))-

Base Information

Chemical Name:5,11-Methanofuro(3,4-d)(3)benzoxonin-1,12(3H,5H)-dione, 6,6a,7,8,9,10,10a,11-octahydro-6,6a-dihydroxy-11,13-dimethyl-3-methylene-, (5R-(5R*,6S*,6aR*,10aR*,11S*,13R*))-
CAS No.:156980-57-3
Molecular Formula:C18H22 O6
Molecular Weight:334.3637
Hs Code.:
DSSTox Substance ID:DTXSID50935575
Wikidata:Q82911649

5,11-Methanofuro(3,4-d)(3)benzoxonin-1,12(3H,5H)-dione, 6,6a,7,8,9,10,10a,11-octahydro-6,6a-dihydroxy-11,13-dimethyl-3-methylene-, (5R-(5R*,6S*,6aR*,10aR*,11S*,13R*))-

Synonyms:tetrodecamycin

Suppliers and Price of 5,11-Methanofuro(3,4-d)(3)benzoxonin-1,12(3H,5H)-dione, 6,6a,7,8,9,10,10a,11-octahydro-6,6a-dihydroxy-11,13-dimethyl-3-methylene-, (5R-(5R*,6S*,6aR*,10aR*,11S*,13R*))-

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 5,11-Methanofuro(3,4-d)(3)benzoxonin-1,12(3H,5H)-dione, 6,6a,7,8,9,10,10a,11-octahydro-6,6a-dihydroxy-11,13-dimethyl-3-methylene-, (5R-(5R*,6S*,6aR*,10aR*,11S*,13R*))-

Chemical Property:

Vapor Pressure:3.49E-12mmHg at 25°C
Boiling Point:502.1°C at 760 mmHg
Flash Point:181.4°C
Density:1.38g/cm³
XLogP3:1.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:0
Exact Mass:334.14163842
Heavy Atom Count:24
Complexity:694

Purity/Quality:: 95% ^*data from raw suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Canonical SMILES:CC1C2C(C3(CCCCC3C1(C(=O)C4=C(O2)C(=C)OC4=O)C)O)O

Technology Process of 5,11-Methanofuro(3,4-d)(3)benzoxonin-1,12(3H,5H)-dione, 6,6a,7,8,9,10,10a,11-octahydro-6,6a-dihydroxy-11,13-dimethyl-3-methylene-, (5R-(5R*,6S*,6aR*,10aR*,11S*,13R*))-

There total 23 articles about 5,11-Methanofuro(3,4-d)(3)benzoxonin-1,12(3H,5H)-dione, 6,6a,7,8,9,10,10a,11-octahydro-6,6a-dihydroxy-11,13-dimethyl-3-methylene-, (5R-(5R*,6S*,6aR*,10aR*,11S*,13R*))- 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: 63.0%

: 892867-56-0
C₁₇H₂₂O₆

: 33797-51-2
eschenmoser's salt

: 156980-57-3
(-)-tetrodecamycin

Guidance literature:: C₁₇H₂₂O₆; eschenmoser's salt; With N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; at 20 ℃; for 12h;

With methyl iodide; In 1,4-dioxane; at 20 ℃; for 11h;
DOI:10.1016/j.tetlet.2006.03.078

Reference yield:

: (3S,4S,5S)-3,4-Dimethyl-5-trityloxymethyl-dihydro-furan-2-one

: 156980-57-3
(-)-tetrodecamycin

Guidance literature:: Multi-step reaction with 21 steps

1.1: LDA / tetrahydrofuran / 0.17 h / -78 °C

1.2: 91 percent / SOCl₂; pyridine / 1 h / 0 °C

2.1: LiBH₄ / tetrahydrofuran / 38 h / 65 °C

3.1: K₂CO₃; 18-crown-6-ether / acetonitrile / 8 h / 50 °C

4.1: DBU / acetonitrile / 20 h / 65 °C

5.1: 86 percent / SeO₂ / dioxane; H₂O / 17 h / 90 °C

6.1: 77 percent / NaBH₄; NiCl₂*6H₂O / methanol; CH₂Cl₂ / 0.17 h / 0 °C

7.1: Et₂AlCl / CH₂Cl₂ / 0.5 h / -78 - 0 °C

8.1: PCC; Al₂O₃ / CH₂Cl₂ / 6 h / 20 °C

9.1: SmI₂; t-BuOH / tetrahydrofuran / 0.5 h / -78 °C

10.1: PPTS / CH₂Cl₂ / 8 h / 20 °C

11.1: TBAF / tetrahydrofuran / 15 h / 50 °C

12.1: 75 percent / KH / 1,2-dichloro-ethane / 6 h / 75 °C

13.1: hydrogen / Pd/C / ethanol / 2 h / 20 °C

14.1: PCC; Al₂O₃ / CH₂Cl₂ / 6 h / 20 °C

15.1: NaHMDS / tetrahydrofuran / 0.17 h / -78 °C

15.2: 81 percent / IBX / toluene; dimethylsulfoxide / 3 h / 20 °C

16.1: 91 percent / aq. Na₂CO₃ / tetrahydrofuran / 15 h / 20 °C

17.1: 74 percent / WSCl*HCl; pyridine / CH₂Cl₂ / 1 h / 20 °C

18.1: 80 percent / Et₃SiH / Lindlar catalyst / acetone / 0.5 h / 20 °C

19.1: 75 percent / CBr₄; PPh₃ / CH₂Cl₂ / 0.5 h / 20 °C

20.1: 85 percent / aq. TFA / 10 h / 50 °C

21.1: i-Pr₂NEt / dioxane / 12 h / 20 °C

21.2: 63 percent / MeI / dioxane / 11 h / 20 °C

With pyridine; triethylsilane; aluminum oxide; sodium tetrahydroborate; lithium borohydride; selenium(IV) oxide; samarium diiodide; 18-crown-6 ether; carbon tetrabromide; WSCl*HCl; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; diethylaluminium chloride; pyridinium p-toluenesulfonate; potassium hydride; sodium carbonate; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; triphenylphosphine; pyridinium chlorochromate; trifluoroacetic acid; nickel dichloride; tert-butyl alcohol; lithium diisopropyl amide; palladium on activated charcoal; Lindlar's catalyst; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; 1,2-dichloro-ethane; acetone; acetonitrile; 12.1: Michael addition;
DOI:10.1016/j.tetlet.2006.03.078

Reference yield:

: 892867-38-8
(3R,4S,5S)-3-Cyclohex-1-enyl-3,4-dimethyl-5-trityloxymethyl-dihydro-furan-2-one

: 156980-57-3
(-)-tetrodecamycin

Guidance literature:: Multi-step reaction with 20 steps

1.1: LiBH₄ / tetrahydrofuran / 38 h / 65 °C

2.1: K₂CO₃; 18-crown-6-ether / acetonitrile / 8 h / 50 °C

3.1: DBU / acetonitrile / 20 h / 65 °C

4.1: 86 percent / SeO₂ / dioxane; H₂O / 17 h / 90 °C

5.1: 77 percent / NaBH₄; NiCl₂*6H₂O / methanol; CH₂Cl₂ / 0.17 h / 0 °C

6.1: Et₂AlCl / CH₂Cl₂ / 0.5 h / -78 - 0 °C

7.1: PCC; Al₂O₃ / CH₂Cl₂ / 6 h / 20 °C

8.1: SmI₂; t-BuOH / tetrahydrofuran / 0.5 h / -78 °C

9.1: PPTS / CH₂Cl₂ / 8 h / 20 °C

10.1: TBAF / tetrahydrofuran / 15 h / 50 °C

11.1: 75 percent / KH / 1,2-dichloro-ethane / 6 h / 75 °C

12.1: hydrogen / Pd/C / ethanol / 2 h / 20 °C

13.1: PCC; Al₂O₃ / CH₂Cl₂ / 6 h / 20 °C

14.1: NaHMDS / tetrahydrofuran / 0.17 h / -78 °C

14.2: 81 percent / IBX / toluene; dimethylsulfoxide / 3 h / 20 °C

15.1: 91 percent / aq. Na₂CO₃ / tetrahydrofuran / 15 h / 20 °C

16.1: 74 percent / WSCl*HCl; pyridine / CH₂Cl₂ / 1 h / 20 °C

17.1: 80 percent / Et₃SiH / Lindlar catalyst / acetone / 0.5 h / 20 °C

18.1: 75 percent / CBr₄; PPh₃ / CH₂Cl₂ / 0.5 h / 20 °C

19.1: 85 percent / aq. TFA / 10 h / 50 °C

20.1: i-Pr₂NEt / dioxane / 12 h / 20 °C

20.2: 63 percent / MeI / dioxane / 11 h / 20 °C

With pyridine; triethylsilane; aluminum oxide; sodium tetrahydroborate; lithium borohydride; selenium(IV) oxide; samarium diiodide; 18-crown-6 ether; carbon tetrabromide; WSCl*HCl; tetrabutyl ammonium fluoride; hydrogen; sodium hexamethyldisilazane; diethylaluminium chloride; pyridinium p-toluenesulfonate; potassium hydride; sodium carbonate; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; triphenylphosphine; pyridinium chlorochromate; trifluoroacetic acid; nickel dichloride; tert-butyl alcohol; palladium on activated charcoal; Lindlar's catalyst; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; 1,2-dichloro-ethane; acetone; acetonitrile; 11.1: Michael addition;
DOI:10.1016/j.tetlet.2006.03.078