(-)-{(2R,3S,4aS,6aR,7S,10aS,11aR)-3-[(1-(benzyloxy)-1-methylethyl]-2,3,4a,5,6,6a,7,8,9,10-decahydro-6a,7-dimethyl-7-[5-3-methylbut-2-enyl)-1H-indol-2-yl]-2-[(triethylsilyl)oxy]-1H-benzo[f]oxireno[2,3-e][1]benzopyran-8-yl}methanol

Base Information

Chemical Name:(-)-{(2R,3S,4aS,6aR,7S,10aS,11aR)-3-[(1-(benzyloxy)-1-methylethyl]-2,3,4a,5,6,6a,7,8,9,10-decahydro-6a,7-dimethyl-7-[5-3-methylbut-2-enyl)-1H-indol-2-yl]-2-[(triethylsilyl)oxy]-1H-benzo[f]oxireno[2,3-e][1]benzopyran-8-yl}methanol
CAS No.:502614-04-2
Molecular Formula:C₄₅H₆₅NO₅Si
Molecular Weight:728.1
Hs Code.:

(-)-{(2R,3S,4aS,6aR,7S,10aS,11aR)-3-[(1-(benzyloxy)-1-methylethyl]-2,3,4a,5,6,6a,7,8,9,10-decahydro-6a,7-dimethyl-7-[5-3-methylbut-2-enyl)-1H-indol-2-yl]-2-[(triethylsilyl)oxy]-1H-benzo[f]oxireno[2,3-e][1]benzopyran-8-yl}methanol

Synonyms:(-)-{(2R,3S,4aS,6aR,7S,10aS,11aR)-3-[(1-(benzyloxy)-1-methylethyl]-2,3,4a,5,6,6a,7,8,9,10-decahydro-6a,7-dimethyl-7-[5-3-methylbut-2-enyl)-1H-indol-2-yl]-2-[(triethylsilyl)oxy]-1H-benzo[f]oxireno[2,3-e][1]benzopyran-8-yl}methanol

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Chemical Property of (-)-{(2R,3S,4aS,6aR,7S,10aS,11aR)-3-[(1-(benzyloxy)-1-methylethyl]-2,3,4a,5,6,6a,7,8,9,10-decahydro-6a,7-dimethyl-7-[5-3-methylbut-2-enyl)-1H-indol-2-yl]-2-[(triethylsilyl)oxy]-1H-benzo[f]oxireno[2,3-e][1]benzopyran-8-yl}methanol

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Technology Process of (-)-{(2R,3S,4aS,6aR,7S,10aS,11aR)-3-[(1-(benzyloxy)-1-methylethyl]-2,3,4a,5,6,6a,7,8,9,10-decahydro-6a,7-dimethyl-7-[5-3-methylbut-2-enyl)-1H-indol-2-yl]-2-[(triethylsilyl)oxy]-1H-benzo[f]oxireno[2,3-e][1]benzopyran-8-yl}methanol

There total 33 articles about (-)-{(2R,3S,4aS,6aR,7S,10aS,11aR)-3-[(1-(benzyloxy)-1-methylethyl]-2,3,4a,5,6,6a,7,8,9,10-decahydro-6a,7-dimethyl-7-[5-3-methylbut-2-enyl)-1H-indol-2-yl]-2-[(triethylsilyl)oxy]-1H-benzo[f]oxireno[2,3-e][1]benzopyran-8-yl}methanol 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: 76.0%

: 502613-88-9
2-methyl-4-(3-methylbut-2-enyl)benzeneamine

: 502613-89-0
(-)-(2S,3R,4aR,5aS,10aS,10bR,12aS)-2-[1-(benzyloxy)-1-methylethyl]-3,4,6,7,7a,8,10,10a,10b,11,12,12a-dodecahydro-10a,10b-dimethyl-3-[(triethylsilyl)oxy]-2H-[2]benzofuro[5,4-f]oxireno[2,3-e][1]benzopyran-10-one

: 502614-04-2
(-)-{(2R,3S,4aS,6aR,7S,10aS,11aR)-3-[(1-(benzyloxy)-1-methylethyl]-2,3,4a,5,6,6a,7,8,9,10-decahydro-6a,7-dimethyl-7-[5-3-methylbut-2-enyl)-1H-indol-2-yl]-2-[(triethylsilyl)oxy]-1H-benzo[f]oxireno[2,3-e][1]benzopyran-8-yl}methanol

Guidance literature:: 2-methyl-4-(3-methylbut-2-enyl)benzeneamine; With chloro-trimethyl-silane; methyllithium; In diethyl ether; at 0 ℃; for 1.5h;

(-)-(2S,3R,4aR,5aS,10aS,10bR,12aS)-2-[1-(benzyloxy)-1-methylethyl]-3,4,6,7,7a,8,10,10a,10b,11,12,12a-dodecahydro-10a,10b-dimethyl-3-[(triethylsilyl)oxy]-2H-[2]benzofuro[5,4-f]oxireno[2,3-e][1]benzopyran-10-one; In diethyl ether; at 0 - 20 ℃; for 0.416667h;

In toluene; for 40h; Heating;
DOI:10.1002/hlca.200390328

Reference yield:

: 83657-30-1
(+)-(1S)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-hydroxypropan-2-one

: 502614-04-2
(-)-{(2R,3S,4aS,6aR,7S,10aS,11aR)-3-[(1-(benzyloxy)-1-methylethyl]-2,3,4a,5,6,6a,7,8,9,10-decahydro-6a,7-dimethyl-7-[5-3-methylbut-2-enyl)-1H-indol-2-yl]-2-[(triethylsilyl)oxy]-1H-benzo[f]oxireno[2,3-e][1]benzopyran-8-yl}methanol

Guidance literature:: Multi-step reaction with 15 steps

1.1: 90 percent / tetrahydrofuran; diethyl ether / 1 h / 20 °C

2.1: 58 percent / AcOH; Ac₂O / 38 h / 20 °C

3.1: 96 percent / NaH; Bu₄NI / tetrahydrofuran / 0 - 20 °C

4.1: 90 percent / (+)-camphorsulfonic acid / methanol; H₂O / 2.5 h / 65 °C

5.1: 91 percent / NaH; 1-tosyl-1H-imidazole / tetrahydrofuran / -78 - 0 °C / 2.2 Torr

6.1: LiNEt₂; DMPU; chiral octahydronaphthalene dimethylhydrazone / tetrahydrofuran; hexane / 17 h / -40 - 65 °C

7.1: DMAP / CH₂Cl₂ / 18 h / 20 °C

8.1: 615 mg / AcONa; AcOH / benzene / 45 h / 65 °C

9.1: 70 percent / aq. HClO₄ / acetonitrile / 1.25 h / 55 °C

10.1: 91 percent / N-iodosuccinimide; tetrabutylammonium iodide / CH₂Cl₂ / 1 h / 0 - 20 °C

11.1: 81 percent / Et₃SiH; TfOH / acetonitrile; CH₂Cl₂ / 1 h / -50 - -20 °C

12.1: 77 percent / m-CPBA; NaHCO₃ / toluene / 48 h / 20 °C

13.1: KOH / methanol; H₂O / 42 h / Heating

13.2: 91 percent / DMAP; EDCI / CH₂Cl₂ / 0.33 h / 20 °C

14.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 0.33 h / 20 °C

15.1: MeLi; TMSCl / diethyl ether / 1.5 h / 0 °C

15.2: diethyl ether / 0.42 h / 0 - 20 °C

15.3: 76 percent / toluene / 40 h / Heating

With 2,6-dimethylpyridine; triethylsilane; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; potassium hydroxide; N-iodo-succinimide; chloro-trimethyl-silane; perchloric acid; trifluorormethanesulfonic acid; chiral octahydronaphthalene dimethylhydrazone; lithium diethylamide; methyllithium; sodium acetate; acetic anhydride; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; acetic acid; (+)-10-camphorsulfonic acid; 3-chloro-benzenecarboperoxoic acid; N-tosylimidazole; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; toluene; acetonitrile; benzene;
DOI:10.1002/hlca.200390328

Reference yield:

: 502614-16-6
(+)-(1S)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-methyl-1-[(methylsulfanyl)methoxy]propan-2-ol

: 502614-04-2
(-)-{(2R,3S,4aS,6aR,7S,10aS,11aR)-3-[(1-(benzyloxy)-1-methylethyl]-2,3,4a,5,6,6a,7,8,9,10-decahydro-6a,7-dimethyl-7-[5-3-methylbut-2-enyl)-1H-indol-2-yl]-2-[(triethylsilyl)oxy]-1H-benzo[f]oxireno[2,3-e][1]benzopyran-8-yl}methanol

Guidance literature:: Multi-step reaction with 13 steps

1.1: 96 percent / NaH; Bu₄NI / tetrahydrofuran / 0 - 20 °C

2.1: 90 percent / (+)-camphorsulfonic acid / methanol; H₂O / 2.5 h / 65 °C

3.1: 91 percent / NaH; 1-tosyl-1H-imidazole / tetrahydrofuran / -78 - 0 °C / 2.2 Torr

4.1: LiNEt₂; DMPU; chiral octahydronaphthalene dimethylhydrazone / tetrahydrofuran; hexane / 17 h / -40 - 65 °C

5.1: DMAP / CH₂Cl₂ / 18 h / 20 °C

6.1: 615 mg / AcONa; AcOH / benzene / 45 h / 65 °C

7.1: 70 percent / aq. HClO₄ / acetonitrile / 1.25 h / 55 °C

8.1: 91 percent / N-iodosuccinimide; tetrabutylammonium iodide / CH₂Cl₂ / 1 h / 0 - 20 °C

9.1: 81 percent / Et₃SiH; TfOH / acetonitrile; CH₂Cl₂ / 1 h / -50 - -20 °C

10.1: 77 percent / m-CPBA; NaHCO₃ / toluene / 48 h / 20 °C

11.1: KOH / methanol; H₂O / 42 h / Heating

11.2: 91 percent / DMAP; EDCI / CH₂Cl₂ / 0.33 h / 20 °C

12.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 0.33 h / 20 °C

13.1: MeLi; TMSCl / diethyl ether / 1.5 h / 0 °C

13.2: diethyl ether / 0.42 h / 0 - 20 °C

13.3: 76 percent / toluene / 40 h / Heating

With 2,6-dimethylpyridine; triethylsilane; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; potassium hydroxide; N-iodo-succinimide; chloro-trimethyl-silane; perchloric acid; trifluorormethanesulfonic acid; chiral octahydronaphthalene dimethylhydrazone; lithium diethylamide; methyllithium; sodium acetate; tetra-(n-butyl)ammonium iodide; sodium hydride; sodium hydrogencarbonate; acetic acid; (+)-10-camphorsulfonic acid; 3-chloro-benzenecarboperoxoic acid; N-tosylimidazole; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; toluene; acetonitrile; benzene;
DOI:10.1002/hlca.200390328