(8S,9S,12S)-4,5-didehydro-4-phenylthiomethyl-17,18,19-trisnoraphidicolin-3,16-dione 16,16-ethylene acetal

Base Information

Chemical Name:(8S,9S,12S)-4,5-didehydro-4-phenylthiomethyl-17,18,19-trisnoraphidicolin-3,16-dione 16,16-ethylene acetal
CAS No.:181230-67-1
Molecular Formula:C₂₆H₃₂O₃S
Molecular Weight:424.604
Hs Code.:

Synonyms:(8S,9S,12S)-4,5-didehydro-4-phenylthiomethyl-17,18,19-trisnoraphidicolin-3,16-dione 16,16-ethylene acetal

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Chemical Property of (8S,9S,12S)-4,5-didehydro-4-phenylthiomethyl-17,18,19-trisnoraphidicolin-3,16-dione 16,16-ethylene acetal

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Technology Process of (8S,9S,12S)-4,5-didehydro-4-phenylthiomethyl-17,18,19-trisnoraphidicolin-3,16-dione 16,16-ethylene acetal

There total 17 articles about (8S,9S,12S)-4,5-didehydro-4-phenylthiomethyl-17,18,19-trisnoraphidicolin-3,16-dione 16,16-ethylene acetal 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: 95.0%

: 50-00-0,30525-89-4,61233-19-0
formaldehyd

: 108-98-5
thiophenol

: 166940-35-8
(8S,9S,12S)-4,5-didehydro-17,18,19-trisnoraphidicolin-3,16-dione 16,16-ethylene acetal

: 181230-67-1
(8S,9S,12S)-4,5-didehydro-4-phenylthiomethyl-17,18,19-trisnoraphidicolin-3,16-dione 16,16-ethylene acetal

Guidance literature:: With triethylamine; In ethanol; for 48h; Heating;
DOI:10.1016/0040-4020(96)00575-3

Reference yield:

: (1R,2R)-4-tert-butyldimethylsiloxy-4-ethylidene-2-(2-propenyl)cyclohexane

: 181230-67-1
(8S,9S,12S)-4,5-didehydro-4-phenylthiomethyl-17,18,19-trisnoraphidicolin-3,16-dione 16,16-ethylene acetal

Guidance literature:: Multi-step reaction with 16 steps

1: 83 percent / n-Bu₄N⁽¹⁺⁾*F^(1-) / tetrahydrofuran / 12 h / Ambient temperature

2: 91 percent / 4A-MS, NMO, n-Pr₄N⁽¹⁺⁾*RuO₄^(1-) / CH₂Cl₂ / 1.) 0 deg C, 5 min, 2.) RT, 1 h

3: 100 percent / PPTS / benzene / 2.5 h / Heating

4: 93 percent / O₂, PdCl₂, CuCl / dimethylformamide; H₂O / 5 h / 45 °C

5: 1.) LDA / 1.) THF, hexane, -78 deg C, 50 min, 2.) THF, hexane, a) -78 deg C, 80 min, b) 0 deg C, 10 min

6: 86 percent / LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 45 min, 2.) 0 deg C, 0.5 h

7: 1.) n-BuLi, 2.) BF₃*Et₂O / 1.) THF, hexane, -78 deg C, 1.5 h, 2.) THF, hexane, -78 deg C, 1 h

8: 76 percent / P(o-tolyl)3, (dba)3Pd₂*CHCl₃, AcOH / benzene / 15 h / 60 °C / var. reagents and solvents; var. temp. and reaction time

9: 69 percent / PdCl₂, CuCl, O₂ / dimethylformamide; H₂O / 11 h / 60 °C

10: 96 percent / H₂ / 10percent Pd-C / ethanol / 5 h / Ambient temperature

11: 1.) n-BuLi / 1.) DME, hexane, reflux, 2.5 h, 2.) DME, hexane, RT, 7 h

12: 78 percent / NMO, 4A-MS, n-Pr₄N⁽¹⁺⁾*RuO₄^(1-) / CH₂Cl₂ / 1 h / Ambient temperature

13: 1.) n-BuLi, HPMA / 1.) THF, hexane, -78 deg C, 0.5 h, 2.) THF, hexane, a) -78 deg C, 10 min, b) 0 deg C, 0.5 h, c) RT, 2 h

14: 70 percent / methylene blue / toluene / 190 h / 220 °C

15: 1.) hematoporphiryn, O₂, pyridine, 2.) NaI, 3.) NMO, 4A-MS, n-Pr₄N⁽¹⁺⁾*RuO₄^(1-)

16: 95 percent / Et₃N / ethanol / 48 h / Heating

With pyridine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 13,17-bis(2-carboxylatoethyl)-3,8-bis[1-hydroxyethyl]-2,7,12,18-tetramethylporphine; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; hydrogen; oxygen; methylene blue; pyridinium p-toluenesulfonate; acetic acid; triethylamine; tris-(o-tolyl)phosphine; sodium iodide; copper(l) chloride; palladium dichloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1016/0040-4020(96)00575-3

Reference yield:

: (1R,2R)-4-ethylidene-2-(2-propenyl)cyclohexanol

: 181230-67-1
(8S,9S,12S)-4,5-didehydro-4-phenylthiomethyl-17,18,19-trisnoraphidicolin-3,16-dione 16,16-ethylene acetal

Guidance literature:: Multi-step reaction with 15 steps

1: 91 percent / 4A-MS, NMO, n-Pr₄N⁽¹⁺⁾*RuO₄^(1-) / CH₂Cl₂ / 1.) 0 deg C, 5 min, 2.) RT, 1 h

2: 100 percent / PPTS / benzene / 2.5 h / Heating

3: 93 percent / O₂, PdCl₂, CuCl / dimethylformamide; H₂O / 5 h / 45 °C

4: 1.) LDA / 1.) THF, hexane, -78 deg C, 50 min, 2.) THF, hexane, a) -78 deg C, 80 min, b) 0 deg C, 10 min

5: 86 percent / LDA / tetrahydrofuran; hexane / 1.) -78 deg C, 45 min, 2.) 0 deg C, 0.5 h

6: 1.) n-BuLi, 2.) BF₃*Et₂O / 1.) THF, hexane, -78 deg C, 1.5 h, 2.) THF, hexane, -78 deg C, 1 h

7: 76 percent / P(o-tolyl)3, (dba)3Pd₂*CHCl₃, AcOH / benzene / 15 h / 60 °C / var. reagents and solvents; var. temp. and reaction time

8: 69 percent / PdCl₂, CuCl, O₂ / dimethylformamide; H₂O / 11 h / 60 °C

9: 96 percent / H₂ / 10percent Pd-C / ethanol / 5 h / Ambient temperature

10: 1.) n-BuLi / 1.) DME, hexane, reflux, 2.5 h, 2.) DME, hexane, RT, 7 h

11: 78 percent / NMO, 4A-MS, n-Pr₄N⁽¹⁺⁾*RuO₄^(1-) / CH₂Cl₂ / 1 h / Ambient temperature

12: 1.) n-BuLi, HPMA / 1.) THF, hexane, -78 deg C, 0.5 h, 2.) THF, hexane, a) -78 deg C, 10 min, b) 0 deg C, 0.5 h, c) RT, 2 h

13: 70 percent / methylene blue / toluene / 190 h / 220 °C

14: 1.) hematoporphiryn, O₂, pyridine, 2.) NaI, 3.) NMO, 4A-MS, n-Pr₄N⁽¹⁺⁾*RuO₄^(1-)

15: 95 percent / Et₃N / ethanol / 48 h / Heating

With pyridine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 13,17-bis(2-carboxylatoethyl)-3,8-bis[1-hydroxyethyl]-2,7,12,18-tetramethylporphine; boron trifluoride diethyl etherate; hydrogen; oxygen; methylene blue; pyridinium p-toluenesulfonate; acetic acid; triethylamine; tris-(o-tolyl)phosphine; sodium iodide; copper(l) chloride; palladium dichloride; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1016/0040-4020(96)00575-3