(-)-(2S,3R,4aR,5aS,13bS,13cR,15aS)-2-[1-(benzyloxy)-1-methylethyl]-3,4,5,6,7,7a,8,13,13b,13c,14,15,15a-dodecahydro-13b,13c-dimethyl-10-(3-methylbut-2-enyl)-3-[(triethylsilyl)oxy]-2H-oxireno[2'',3'':4a',5'][1]benzopyrano[5'6':6,7]indeno[1,2-b]indole

Base Information

• Chemical Name: (-)-(2S,3R,4aR,5aS,13bS,13cR,15aS)-2-[1-(benzyloxy)-1-methylethyl]-3,4,5,6,7,7a,8,13,13b,13c,14,15,15a-dodecahydro-13b,13c-dimethyl-10-(3-methylbut-2-enyl)-3-[(triethylsilyl)oxy]-2H-oxireno[2'',3'':4a',5'][1]benzopyrano[5'6':6,7]indeno[1,2-b]indole
• CAS No.: 502614-06-4
• Molecular Formula: C₄₅H₆₃NO₄Si
• Molecular Weight: 710.085
• Mol file: 502614-06-4.mol

Synonyms:(-)-(2S,3R,4aR,5aS,13bS,13cR,15aS)-2-[1-(benzyloxy)-1-methylethyl]-3,4,5,6,7,7a,8,13,13b,13c,14,15,15a-dodecahydro-13b,13c-dimethyl-10-(3-methylbut-2-enyl)-3-[(triethylsilyl)oxy]-2H-oxireno[2'',3'':4a',5'][1]benzopyrano[5'6':6,7]indeno[1,2-b]indole

Chemical Property of (-)-(2S,3R,4aR,5aS,13bS,13cR,15aS)-2-[1-(benzyloxy)-1-methylethyl]-3,4,5,6,7,7a,8,13,13b,13c,14,15,15a-dodecahydro-13b,13c-dimethyl-10-(3-methylbut-2-enyl)-3-[(triethylsilyl)oxy]-2H-oxireno[2'',3'':4a',5'][1]benzopyrano[5'6':6,7]indeno[1,2-b]indole

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(2S,3R,4aR,5aS,13bS,13cR,15aS)-2-[1-(benzyloxy)-1-methylethyl]-3,4,5,6,7,7a,8,13,13b,13c,14,15,15a-dodecahydro-13b,13c-dimethyl-10-(3-methylbut-2-enyl)-3-[(triethylsilyl)oxy]-2H-oxireno[2'',3'':4a',5'][1]benzopyrano[5'6':6,7]indeno[1,2-b]indole

There total 33 articles about (-)-(2S,3R,4aR,5aS,13bS,13cR,15aS)-2-[1-(benzyloxy)-1-methylethyl]-3,4,5,6,7,7a,8,13,13b,13c,14,15,15a-dodecahydro-13b,13c-dimethyl-10-(3-methylbut-2-enyl)-3-[(triethylsilyl)oxy]-2H-oxireno[2'',3'':4a',5'][1]benzopyrano[5'6':6,7]indeno[1,2-b]indole 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: 73.0%

(-)-{(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}methyl metanesulfonate (502614-05-3) → (-)-(2S,3R,4aR,5aS,13bS,13cR,15aS)-2-[1-(benzyloxy)-1-methylethyl]-3,4,5,6,7,7a,8,13,13b,13c,14,15,15a-dodecahydro-13b,13c-dimethyl-10-(3-methylbut-2-enyl)-3-[(triethylsilyl)oxy]-2H-oxireno[2'',3'':4a',5'][1]benzopyrano[5'6':6,7]indeno[1,2-b]indole (502614-06-4)

Guidance literature:

With tert-butylmagnesium chloride; In toluene; at 110 ℃; for 0.0833333h;

DOI:10.1002/hlca.200390328

Reference yield:

(+)-(1S)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-1-hydroxypropan-2-one (83657-30-1) → (-)-(2S,3R,4aR,5aS,13bS,13cR,15aS)-2-[1-(benzyloxy)-1-methylethyl]-3,4,5,6,7,7a,8,13,13b,13c,14,15,15a-dodecahydro-13b,13c-dimethyl-10-(3-methylbut-2-enyl)-3-[(triethylsilyl)oxy]-2H-oxireno[2'',3'':4a',5'][1]benzopyrano[5'6':6,7]indeno[1,2-b]indole (502614-06-4)

Guidance literature:

Multi-step reaction with 17 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

16.1: 90 percent / DMAP / CH₂Cl₂ / 0.33 h / 0 - 20 °C

17.1: 73 percent / tBuMgCl / toluene / 0.08 h / 110 °C

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; tert-butylmagnesium chloride; 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:

(+)-(1S)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-methyl-1-[(methylsulfanyl)methoxy]propan-2-ol (502614-16-6) → (-)-(2S,3R,4aR,5aS,13bS,13cR,15aS)-2-[1-(benzyloxy)-1-methylethyl]-3,4,5,6,7,7a,8,13,13b,13c,14,15,15a-dodecahydro-13b,13c-dimethyl-10-(3-methylbut-2-enyl)-3-[(triethylsilyl)oxy]-2H-oxireno[2'',3'':4a',5'][1]benzopyrano[5'6':6,7]indeno[1,2-b]indole (502614-06-4)

Guidance literature:

Multi-step reaction with 15 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

14.1: 90 percent / DMAP / CH₂Cl₂ / 0.33 h / 0 - 20 °C

15.1: 73 percent / tBuMgCl / toluene / 0.08 h / 110 °C

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; tert-butylmagnesium chloride; 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

upstream raw materials:

(-)-{(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}methyl metanesulfonate

4-bromo-2-methyl-N,N-bis(trimethylsilyl)benzeneamine

(2R,3R)-1,2-O-isopropylidene-4-methyl-4-pentene-1,2,3-triol

4-Bromo-2-methylaniline

Downstream raw materials:

(-)-(2S,3R,4aR,5aS,13bS,13cR,15aS)-2-[1-(benzyloxy)-1-methylethyl]-3,4,5,6,7,7a,8,13,13b,13c,14,15,15a-dodecahydro-13b,13c-dimethyl-10-(3-methylbut-2-enyl)-2H-oxireno[2'',3'':4a',5'][1]benzopyrano[5'6':6,7]indeno[1,2-b]indol-3-ol

Refernces

• 1、 Smith 3rd., Amos B,Cui, Haifeng. "Total synthesis of (-)-21-isopentenylpaxilline.". . p. 587 - 590. Retrieved 2007/10/03.