myrocin C

Base Information

Chemical Name:myrocin C
CAS No.:113122-50-2
Molecular Formula:C₂₀H₂₄O₅
Molecular Weight:344.408
Hs Code.:
Mol file:113122-50-2.mol

Synonyms:3H-Cyclopropa[4,4a]phenanthro[10,1-bc]furan-3,5(1H)-dione,7-ethenyl-2,2a,4a,7,8,9,9a,9c,10,10a-decahydro-4a,9a-dihydroxy-2a,7-dimethyl-,(2aa,4aa,7a,9aa,9bR*,9ca,10aa)-(+)-; Myrocin C

Suppliers and Price of myrocin C

Supply Marketing:

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

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

American Custom Chemicals Corporation
MYROCIN C 95.00%
5MG
$ 501.77

Total 1 raw suppliers

Chemical Property of myrocin C

Chemical Property:

Vapor Pressure:2.72E-13mmHg at 25°C
Boiling Point:526.7°Cat760mmHg
Flash Point:190.3°C
PSA：83.83000
Density:1.29g/cm³
LogP:1.88070

Purity/Quality:: MYROCIN C 95.00% ^*data from reagent suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Technology Process of myrocin C

There total 33 articles about myrocin C 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:

: 143495-25-4
(2aα,4aα,5aR*,8α,8aα,8bα)-(+/-)-6-ethenyl-2a,3,4,4a,5,8,8a,8b-octahydro-8-hydroxy-2a-methyl-2H-cyclopropa<4a,5>naphtho<1,8-bc>furan-2-one

: 113122-50-2,143563-73-9
(+/-)-myrocin C

Guidance literature:: Multi-step reaction with 12 steps

1: 93 percent / DCC, DMAP / CH₂Cl₂ / 1 h / 0 - 20 °C

2: benzene / 13 h / Heating

3: tetrahydrofuran / 0.33 h / -78 - 0 °C

4: DIBAL-H / CH₂Cl₂; toluene / 0.17 h / -48 °C

5: PDC, Celite / CH₂Cl₂ / 5 h

6: 84 percent / iodobenzene diacetate, I₂ / cyclohexane / 0.5 h / Ambient temperature; Irradiation

7: 78 percent / Bu₃SnH, AIBN / 0.33 h / 80 °C

8: Dess-Martin periodinane / CH₂Cl₂ / 0.17 h / Ambient temperature

9: H₂O₂, 3N aq. NaOH / methanol / 0.17 h / Ambient temperature

10: 1.) n-BuLi, Me₃Al / 1.) THF, hexane, 0 deg C, 2.) THF, hexane, 0 deg C, 1 h

11: 56 percent / 3,3-dimethyldioxirane / CH₂Cl₂; acetone / 0.5 h

12: 1.) O₂, t-BuOK, 2.) (EtO)3P / 1.) THF, t-BuOH, -78 deg C, 3 h, 2.) THF, 0 deg C, 10 min

With dmap; sodium hydroxide; dipyridinium dichromate; n-butyllithium; 2,2'-azobis(isobutyronitrile); [bis(acetoxy)iodo]benzene; Celite; potassium tert-butylate; dihydrogen peroxide; iodine; trimethylaluminum; oxygen; tri-n-butyl-tin hydride; 3,3-dimethyldioxirane; diisobutylaluminium hydride; Dess-Martin periodane; dicyclohexyl-carbodiimide; triethyl phosphite; In tetrahydrofuran; methanol; dichloromethane; cyclohexane; acetone; toluene; benzene;
DOI:10.1021/ja00104a002

Reference yield:

: 143495-15-2
Acetic acid (2aS,5R,5aS,6S,8aR,8bR)-5-formyl-2a-methyl-2-oxo-2a,3,4,5,5a,6,8a,8b-octahydro-2H-naphtho[1,8-bc]furan-6-yl ester

: 113122-50-2,143563-73-9
(+/-)-myrocin C

Guidance literature:: Multi-step reaction with 22 steps

1: NaBH₄ / methanol / 0.5 h / 0 °C

2: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

3: NaOMe / methanol / 24 h / Ambient temperature

4: 84 percent / PDC, Celite / CH₂Cl₂ / 20 h / Ambient temperature

5: 82 percent / 30percent aq. H₂O₂, 3 aq. N NaOH / methanol / 5.5 h / -78 - -48 °C

6: 81 percent / NaHMDS / tetrahydrofuran / 0.5 h / -78 °C

7: 54 percent / LiCl, (Ph₃P)2PdCl₂ / tetrahydrofuran / 3.5 h / Heating

8: 96 percent / AcOH, TBAF / tetrahydrofuran / 4 h / 0 - 20 °C

9: 96 percent / DMAP, Et₃N / CH₂Cl₂ / 0.25 h / 0 °C

10: 66 percent / Me₃SnLi / diethyl ether; tetrahydrofuran / 0.08 h / 0 °C

11: 93 percent / DCC, DMAP / CH₂Cl₂ / 1 h / 0 - 20 °C

12: benzene / 13 h / Heating

13: tetrahydrofuran / 0.33 h / -78 - 0 °C

14: DIBAL-H / CH₂Cl₂; toluene / 0.17 h / -48 °C

15: PDC, Celite / CH₂Cl₂ / 5 h

16: 84 percent / iodobenzene diacetate, I₂ / cyclohexane / 0.5 h / Ambient temperature; Irradiation

17: 78 percent / Bu₃SnH, AIBN / 0.33 h / 80 °C

18: Dess-Martin periodinane / CH₂Cl₂ / 0.17 h / Ambient temperature

19: H₂O₂, 3N aq. NaOH / methanol / 0.17 h / Ambient temperature

20: 1.) n-BuLi, Me₃Al / 1.) THF, hexane, 0 deg C, 2.) THF, hexane, 0 deg C, 1 h

21: 56 percent / 3,3-dimethyldioxirane / CH₂Cl₂; acetone / 0.5 h

22: 1.) O₂, t-BuOK, 2.) (EtO)3P / 1.) THF, t-BuOH, -78 deg C, 3 h, 2.) THF, 0 deg C, 10 min

With (trimethylstannyl)lithium; dmap; bis-triphenylphosphine-palladium(II) chloride; sodium hydroxide; sodium tetrahydroborate; dipyridinium dichromate; n-butyllithium; 2,2'-azobis(isobutyronitrile); [bis(acetoxy)iodo]benzene; Celite; potassium tert-butylate; tetrabutyl ammonium fluoride; dihydrogen peroxide; iodine; trimethylaluminum; oxygen; tri-n-butyl-tin hydride; sodium methylate; sodium hexamethyldisilazane; 3,3-dimethyldioxirane; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; triethylamine; dicyclohexyl-carbodiimide; lithium chloride; triethyl phosphite; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; cyclohexane; acetone; toluene; benzene;
DOI:10.1021/ja00104a002

Reference yield:

: (1α,4α,4aα,8aα)-(+/-)-2-<(tert-butyldimethylsilyl)oxy>-1,4,4a,8a-tetrahydro-1-methyl-1,4-ethanonaphthalene-5,8-dione

: 113122-50-2,143563-73-9
(+/-)-myrocin C

Guidance literature:: Multi-step reaction with 27 steps

1: 3,3-dimethyldioxirane / CH₂Cl₂; acetone / 2 h / -78 - 0 °C

2: 67 percent / CeCl₃*7H₂O, NaBH₄ / methanol / 1.5 h / -78 °C

3: 97 percent / DMAP, Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

4: 91 percent / AcOH, TBAF / tetrahydrofuran / 0.5 h

5: aq. NaIO₄ / tetrahydrofuran / 1 h / Ambient temperature

6: NaBH₄ / methanol / 0.5 h / 0 °C

7: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

8: NaOMe / methanol / 24 h / Ambient temperature

9: 84 percent / PDC, Celite / CH₂Cl₂ / 20 h / Ambient temperature

10: 82 percent / 30percent aq. H₂O₂, 3 aq. N NaOH / methanol / 5.5 h / -78 - -48 °C

11: 81 percent / NaHMDS / tetrahydrofuran / 0.5 h / -78 °C

12: 54 percent / LiCl, (Ph₃P)2PdCl₂ / tetrahydrofuran / 3.5 h / Heating

13: 96 percent / AcOH, TBAF / tetrahydrofuran / 4 h / 0 - 20 °C

14: 96 percent / DMAP, Et₃N / CH₂Cl₂ / 0.25 h / 0 °C

15: 66 percent / Me₃SnLi / diethyl ether; tetrahydrofuran / 0.08 h / 0 °C

16: 93 percent / DCC, DMAP / CH₂Cl₂ / 1 h / 0 - 20 °C

17: benzene / 13 h / Heating

18: tetrahydrofuran / 0.33 h / -78 - 0 °C

19: DIBAL-H / CH₂Cl₂; toluene / 0.17 h / -48 °C

20: PDC, Celite / CH₂Cl₂ / 5 h

21: 84 percent / iodobenzene diacetate, I₂ / cyclohexane / 0.5 h / Ambient temperature; Irradiation

22: 78 percent / Bu₃SnH, AIBN / 0.33 h / 80 °C

23: Dess-Martin periodinane / CH₂Cl₂ / 0.17 h / Ambient temperature

24: H₂O₂, 3N aq. NaOH / methanol / 0.17 h / Ambient temperature

25: 1.) n-BuLi, Me₃Al / 1.) THF, hexane, 0 deg C, 2.) THF, hexane, 0 deg C, 1 h

26: 56 percent / 3,3-dimethyldioxirane / CH₂Cl₂; acetone / 0.5 h

27: 1.) O₂, t-BuOK, 2.) (EtO)3P / 1.) THF, t-BuOH, -78 deg C, 3 h, 2.) THF, 0 deg C, 10 min

With (trimethylstannyl)lithium; dmap; bis-triphenylphosphine-palladium(II) chloride; sodium hydroxide; sodium tetrahydroborate; sodium periodate; dipyridinium dichromate; n-butyllithium; cerium(III) chloride; 2,2'-azobis(isobutyronitrile); [bis(acetoxy)iodo]benzene; Celite; potassium tert-butylate; tetrabutyl ammonium fluoride; dihydrogen peroxide; iodine; trimethylaluminum; oxygen; tri-n-butyl-tin hydride; sodium methylate; sodium hexamethyldisilazane; 3,3-dimethyldioxirane; diisobutylaluminium hydride; Dess-Martin periodane; acetic acid; triethylamine; dicyclohexyl-carbodiimide; lithium chloride; triethyl phosphite; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; cyclohexane; acetone; toluene; benzene;
DOI:10.1021/ja00104a002