Acetic acid (3aR,4S,6aR,8S,10aR)-4-methyl-3,5-dioxo-4-((1R,2R,4S,6R)-3-oxo-6-phenyl-bicyclo[2.2.1]hept-2-yl)-decahydro-2-oxa-cyclopenta[d]naphthalen-8-yl ester

Base Information

Chemical Name:Acetic acid (3aR,4S,6aR,8S,10aR)-4-methyl-3,5-dioxo-4-((1R,2R,4S,6R)-3-oxo-6-phenyl-bicyclo[2.2.1]hept-2-yl)-decahydro-2-oxa-cyclopenta[d]naphthalen-8-yl ester
CAS No.:615249-37-1
Molecular Formula:C₂₈H₃₂O₆
Molecular Weight:464.558
Hs Code.:

Acetic acid (3aR,4S,6aR,8S,10aR)-4-methyl-3,5-dioxo-4-((1R,2R,4S,6R)-3-oxo-6-phenyl-bicyclo[2.2.1]hept-2-yl)-decahydro-2-oxa-cyclopenta[d]naphthalen-8-yl ester

Synonyms:Acetic acid (3aR,4S,6aR,8S,10aR)-4-methyl-3,5-dioxo-4-((1R,2R,4S,6R)-3-oxo-6-phenyl-bicyclo[2.2.1]hept-2-yl)-decahydro-2-oxa-cyclopenta[d]naphthalen-8-yl ester

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Chemical Property of Acetic acid (3aR,4S,6aR,8S,10aR)-4-methyl-3,5-dioxo-4-((1R,2R,4S,6R)-3-oxo-6-phenyl-bicyclo[2.2.1]hept-2-yl)-decahydro-2-oxa-cyclopenta[d]naphthalen-8-yl ester

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Technology Process of Acetic acid (3aR,4S,6aR,8S,10aR)-4-methyl-3,5-dioxo-4-((1R,2R,4S,6R)-3-oxo-6-phenyl-bicyclo[2.2.1]hept-2-yl)-decahydro-2-oxa-cyclopenta[d]naphthalen-8-yl ester

There total 27 articles about Acetic acid (3aR,4S,6aR,8S,10aR)-4-methyl-3,5-dioxo-4-((1R,2R,4S,6R)-3-oxo-6-phenyl-bicyclo[2.2.1]hept-2-yl)-decahydro-2-oxa-cyclopenta[d]naphthalen-8-yl ester 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: 81.0%

: 615249-29-1
C₂₉H₃₄O₆

: 615249-37-1
Acetic acid (3aR,4S,6aR,8S,10aR)-4-methyl-3,5-dioxo-4-((1R,2R,4S,6R)-3-oxo-6-phenyl-bicyclo[2.2.1]hept-2-yl)-decahydro-2-oxa-cyclopenta[d]naphthalen-8-yl ester

Guidance literature:: With sulfuric acid; In dichloromethane; at 0 ℃; for 0.166667h;
DOI:10.1002/anie.200351744

Reference yield:

: 154278-40-7
(1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-yl acetate

: 615249-37-1
Acetic acid (3aR,4S,6aR,8S,10aR)-4-methyl-3,5-dioxo-4-((1R,2R,4S,6R)-3-oxo-6-phenyl-bicyclo[2.2.1]hept-2-yl)-decahydro-2-oxa-cyclopenta[d]naphthalen-8-yl ester

Guidance literature:: Multi-step reaction with 10 steps

1: 98 percent / p-TsOH / methanol / 3 h / 25 °C

2: 57 percent / TMSOTf; iPr₂NEt / CH₂Cl₂ / 16 h / -20 - 25 °C

3: 57 percent / Br₂; N,N-dimethylaniline / CH₂Cl₂ / 12 h / -78 - 0 °C

4: 75 percent / nBu₃SnH; AIBN / toluene / 15 h / 110 °C

5: 65 percent / KHMDS / tetrahydrofuran / 1 h / -78 °C

6: 78 percent / Pd(PPh₃)4; Cs₂CO₃ / dimethylformamide; methanol / 1 h / 80 °C

7: TBAF / tetrahydrofuran / 0.5 h / 40 °C

8: DMAP; pyridine / 0.1 h / 25 °C

9: 81 percent / H₂SO₄ / CH₂Cl₂ / 0.17 h / 0 °C

With pyridine; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 2,2'-azobis(isobutyronitrile); trimethylsilyl trifluoromethanesulfonate; sulfuric acid; tetrabutyl ammonium fluoride; bromine; tri-n-butyl-tin hydride; potassium hexamethylsilazane; caesium carbonate; toluene-4-sulfonic acid; N,N-dimethyl-aniline; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 7: Suzuki reaction;
DOI:10.1002/anie.200351744

Reference yield:

: 98770-78-6
(S)-3,4,8,8a-tetrahydro-8a-(hydroxymethyl)-1,6-(2H,7H)-naphthalenedione-1-ethylene acetal

: 615249-37-1
Acetic acid (3aR,4S,6aR,8S,10aR)-4-methyl-3,5-dioxo-4-((1R,2R,4S,6R)-3-oxo-6-phenyl-bicyclo[2.2.1]hept-2-yl)-decahydro-2-oxa-cyclopenta[d]naphthalen-8-yl ester

Guidance literature:: Multi-step reaction with 23 steps

1.1: 85 percent / i-Pr₂NEt / CH₂Cl₂ / 20 h / 25 °C

2.1: 80 percent / Li; liq. NH₃ / 1 h / -78 °C

3.1: 99 percent / NaBH₄ / tetrahydrofuran; ethanol / 3 h / -78 - 25 °C

4.1: 80 percent / imidazole; DMAP / dimethylformamide / 24 h / 25 °C

5.1: PPTS / acetone / 24 h / 65 °C

6.1: KHMDS / tetrahydrofuran / 0.5 h / -78 °C

7.1: 89 percent / PPh₃; Pd(OAc)2; i-Pr₂NEt / dimethylformamide / 12 h / 60 °C / 760 Torr

8.1: 95 percent / DIBAL-H / CH₂Cl₂ / 2 h / -78 - 0 °C

9.1: 65 percent / BH₃*THF / tetrahydrofuran / 12 h / 0 °C

10.1: TEMPO; Br(OAc)2^(1-)*Me₃N(+)-resin / CH₂Cl₂ / 2 h / 25 °C

11.1: pyridine / CH₂Cl₂ / 0.1 h / 25 °C

12.1: NaClO₂; 2-methyl-2-butene; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 2 h / 25 °C

12.2: aq. HCl / dioxane / 16 h / 75 °C

13.1: 72 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 25 °C

14.1: 97 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 3 h / 25 °C

15.1: 78 percent / tetrahydrofuran / 12 h / 25 °C

16.1: 50 percent / SeO₂; t-BuOOH / CH₂Cl₂ / 6 h / 25 °C

17.1: 57 percent / Br₂; N,N-dimethylaniline / CH₂Cl₂ / 12 h / -78 - 0 °C

18.1: 75 percent / nBu₃SnH; AIBN / toluene / 15 h / 110 °C

19.1: 65 percent / KHMDS / tetrahydrofuran / 1 h / -78 °C

20.1: 78 percent / Pd(PPh₃)4; Cs₂CO₃ / dimethylformamide; methanol / 1 h / 80 °C

21.1: TBAF / tetrahydrofuran / 0.5 h / 40 °C

22.1: DMAP; pyridine / 0.1 h / 25 °C

23.1: 81 percent / H₂SO₄ / CH₂Cl₂ / 0.17 h / 0 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; tert.-butylhydroperoxide; dmap; palladium diacetate; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; selenium(IV) oxide; borane-THF; 2-methyl-but-2-ene; 2,2'-azobis(isobutyronitrile); Br(OAc)2^(1-)*Me₃N(+)-resin; sulfuric acid; tetrabutyl ammonium fluoride; ammonia; bromine; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; lithium; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; caesium carbonate; Dess-Martin periodane; N,N-dimethyl-aniline; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol; 2.1: Birch reduction / 14.1: Dess-martin oxidation / 15.1: Wittig reaction / 20.1: Suzuki reaction;
DOI:10.1002/anie.200351744