(1R,2S,4S,5R,10R,11S)-16-acetyl-5-hydroxy-10-methyl-3-oxapentacyclo[9.8.0.02,4.05,10.014,19]nonadeca-7,14(19),15,17-tetraen-9-one

Base Information

Chemical Name:(1R,2S,4S,5R,10R,11S)-16-acetyl-5-hydroxy-10-methyl-3-oxapentacyclo[9.8.0.02,4.05,10.014,19]nonadeca-7,14(19),15,17-tetraen-9-one
CAS No.:40071-61-2
Molecular Formula:C21H22O4
Molecular Weight:338.4
Hs Code.:
DSSTox Substance ID:DTXSID601102267
Nikkaji Number:J17.391F
Mol file:40071-61-2.mol

Synonyms:40071-61-2;DTXSID601102267;Chryseno[5,6-b]oxiren-4(1H)-one, 8-acetyl-4a,4b,5,6,10b,10c,11a,11b-octahydro-11b-hydroxy-4a-methyl-, (4aR,4bS,10bR,10cS,11aS,11bR)-

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Chemical Property of (1R,2S,4S,5R,10R,11S)-16-acetyl-5-hydroxy-10-methyl-3-oxapentacyclo[9.8.0.02,4.05,10.014,19]nonadeca-7,14(19),15,17-tetraen-9-one

Chemical Property:

XLogP3:1.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:1
Exact Mass:338.15180918
Heavy Atom Count:25
Complexity:669

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Canonical SMILES:CC(=O)C1=CC2=C(C=C1)C3C(CC2)C4(C(=O)C=CCC4(C5C3O5)O)C
Isomeric SMILES:CC(=O)C1=CC2=C(C=C1)[C@H]3[C@H](CC2)[C@]4(C(=O)C=CC[C@@]4([C@@H]5[C@H]3O5)O)C

Technology Process of (1R,2S,4S,5R,10R,11S)-16-acetyl-5-hydroxy-10-methyl-3-oxapentacyclo[9.8.0.02,4.05,10.014,19]nonadeca-7,14(19),15,17-tetraen-9-one

There total 21 articles about (1R,2S,4S,5R,10R,11S)-16-acetyl-5-hydroxy-10-methyl-3-oxapentacyclo[9.8.0.02,4.05,10.014,19]nonadeca-7,14(19),15,17-tetraen-9-one 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:

: (1aS,1bR,5aR,5bS,11bR,11cS)-9-(1-Ethoxy-vinyl)-1b-hydroxy-5a-methyl-1b,2,5a,5b,6,7,11b,11c-octahydro-1aH-1-oxa-cyclopropa[g]chrysen-5-one

: 40071-61-2
NIC-10

Guidance literature:: With acetic acid; In dichloromethane; at 25 ℃; for 0.333333h;
DOI:10.1021/ja0024892

Reference yield:

: (2R,4bR)-8-Allyloxy-2-(dimethyl-phenyl-silanyl)-4a-methyl-11-triethylsilanyloxy-2,3,4a,4b,5,6,12,12a-octahydro-1H-chrysen-4-one

: 40071-61-2
NIC-10

Guidance literature:: Multi-step reaction with 21 steps

1.1: 90 percent / LiAlH₄ / diethyl ether / 0.5 h / -78 °C

2.1: 92 percent / i-Pr₂NEt / CH₂Cl₂ / 46 h / 23 °C

3.1: 89 percent / p-TsOH / CH₂Cl₂; methanol / 0.08 h / 23 °C

4.1: LDA / tetrahydrofuran / 0.33 h / -78 °C

5.1: 856 mg / O₂; Pd(OAc)2; 2,6-di-tert-butyl-4-methylpyridine / dimethylsulfoxide / 12 h / 25 °C

6.1: L-selectride / tetrahydrofuran / 0.33 h / -78 °C

7.1: 564 mg / t-BuOOH; VO(acac)2 / CH₂Cl₂; decane / 20 h / 0 °C

8.1: 97 percent / Et₃N; DMAP / CH₂Cl₂ / 3 h / 25 °C

9.1: Pd(Ph₃P)4; Et₂NH / CH₂Cl₂ / 3 h / Heating

10.1: 690 mg / Et₃N / CH₂Cl₂ / 18 h / 23 °C

11.1: H₂; AcOH / Pd/C / ethyl acetate / 7 h / 23 °C / 760.05 Torr

12.1: 560 mg / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 23 °C

13.1: 91 percent / K₂CO₃ / methanol; H₂O; CH₂Cl₂ / 2.5 h / 25 °C

14.1: MgI₂; NaI / CH₂Cl₂; acetonitrile / 0.17 h / 0 °C

15.1: CH₂Cl₂; acetonitrile / 0.17 h / 0 °C

15.2: 72 percent / methanesulfonyl chloride; Et₃N / CH₂Cl₂ / 1.5 h / -66 - 25 °C

16.1: 76 percent / t-BuOOH; VO(acac)2 / CH₂Cl₂; decane / 44 h / 0 °C

17.1: Hg(OAc)2; AcOOH / acetic acid; trifluoroacetic acid / 3 h / 25 °C

18.1: Et₃N; DMAP / CH₂Cl₂ / 0.08 h

19.1: 15 mg / DBU / CH₂Cl₂ / 2 h / 25 °C

20.1: Pd(Ph₃P)4; CuCl; LiCl / dimethylsulfoxide / 23 h / 20 - 60 °C

21.1: 5.0 mg / AcOH / CH₂Cl₂ / 0.33 h / 25 °C

With tert.-butylhydroperoxide; peracetic acid; dmap; palladium diacetate; lithium aluminium tetrahydride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 2,6-di-tert-butyl-4-methylpyridine; bis(acetylacetonate)oxovanadium; mercury(II) diacetate; hydrogen; oxygen; L-Selectride; potassium carbonate; Dess-Martin periodane; toluene-4-sulfonic acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; diethylamine; triethylamine; N-ethyl-N,N-diisopropylamine; sodium iodide; copper(l) chloride; lithium chloride; magnesium iodide; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; decane; dichloromethane; water; acetic acid; dimethyl sulfoxide; ethyl acetate; acetonitrile; trifluoroacetic acid; 20.1: Stille coupling;
DOI:10.1021/ja0024892

Reference yield:

: 303998-25-6
(4bR,8R,10S,10aR,10bS)-2-Allyloxy-10-benzyloxymethoxy-8-(dimethyl-phenyl-silanyl)-10a-methyl-7,8,9,10,10a,10b,11,12-octahydro-4bH-chrysen-5-one

: 40071-61-2
NIC-10

Guidance literature:: Multi-step reaction with 16 steps

1.1: L-selectride / tetrahydrofuran / 0.33 h / -78 °C

2.1: 564 mg / t-BuOOH; VO(acac)2 / CH₂Cl₂; decane / 20 h / 0 °C

3.1: 97 percent / Et₃N; DMAP / CH₂Cl₂ / 3 h / 25 °C

4.1: Pd(Ph₃P)4; Et₂NH / CH₂Cl₂ / 3 h / Heating

5.1: 690 mg / Et₃N / CH₂Cl₂ / 18 h / 23 °C

6.1: H₂; AcOH / Pd/C / ethyl acetate / 7 h / 23 °C / 760.05 Torr

7.1: 560 mg / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 23 °C

8.1: 91 percent / K₂CO₃ / methanol; H₂O; CH₂Cl₂ / 2.5 h / 25 °C

9.1: MgI₂; NaI / CH₂Cl₂; acetonitrile / 0.17 h / 0 °C

10.1: CH₂Cl₂; acetonitrile / 0.17 h / 0 °C

10.2: 72 percent / methanesulfonyl chloride; Et₃N / CH₂Cl₂ / 1.5 h / -66 - 25 °C

11.1: 76 percent / t-BuOOH; VO(acac)2 / CH₂Cl₂; decane / 44 h / 0 °C

12.1: Hg(OAc)2; AcOOH / acetic acid; trifluoroacetic acid / 3 h / 25 °C

13.1: Et₃N; DMAP / CH₂Cl₂ / 0.08 h

14.1: 15 mg / DBU / CH₂Cl₂ / 2 h / 25 °C

15.1: Pd(Ph₃P)4; CuCl; LiCl / dimethylsulfoxide / 23 h / 20 - 60 °C

16.1: 5.0 mg / AcOH / CH₂Cl₂ / 0.33 h / 25 °C

With tert.-butylhydroperoxide; peracetic acid; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; bis(acetylacetonate)oxovanadium; mercury(II) diacetate; hydrogen; L-Selectride; potassium carbonate; Dess-Martin periodane; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; diethylamine; triethylamine; sodium iodide; copper(l) chloride; lithium chloride; magnesium iodide; palladium on activated charcoal; In tetrahydrofuran; methanol; decane; dichloromethane; water; acetic acid; dimethyl sulfoxide; ethyl acetate; acetonitrile; trifluoroacetic acid; 15.1: Stille coupling;
DOI:10.1021/ja0024892