(1R,8R,10R,11R)-3-{5-[6-Bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-6-methoxy-pyrazin-2-yl}-10-hydroxy-8-methoxy-11-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5-aza-tricyclo[6.3.1.0^2,6]dodeca-2⁽⁶⁾,3-dien-7-one

Base Information

• Chemical Name: (1R,8R,10R,11R)-3-{5-[6-Bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-6-methoxy-pyrazin-2-yl}-10-hydroxy-8-methoxy-11-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5-aza-tricyclo[6.3.1.0^2,6]dodeca-2⁽⁶⁾,3-dien-7-one
• CAS No.: 756894-02-7
• Molecular Formula: C₃₉H₄₅BrN₄O₇SSi
• Molecular Weight: 821.864

Synonyms:(1R,8R,10R,11R)-3-{5-[6-Bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-6-methoxy-pyrazin-2-yl}-10-hydroxy-8-methoxy-11-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5-aza-tricyclo[6.3.1.0^2,6]dodeca-2⁽⁶⁾,3-dien-7-one

Chemical Property of (1R,8R,10R,11R)-3-{5-[6-Bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-6-methoxy-pyrazin-2-yl}-10-hydroxy-8-methoxy-11-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5-aza-tricyclo[6.3.1.0^2,6]dodeca-2⁽⁶⁾,3-dien-7-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,8R,10R,11R)-3-{5-[6-Bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-6-methoxy-pyrazin-2-yl}-10-hydroxy-8-methoxy-11-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5-aza-tricyclo[6.3.1.0^2,6]dodeca-2⁽⁶⁾,3-dien-7-one

There total 22 articles about (1R,8R,10R,11R)-3-{5-[6-Bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-6-methoxy-pyrazin-2-yl}-10-hydroxy-8-methoxy-11-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5-aza-tricyclo[6.3.1.0^2,6]dodeca-2⁽⁶⁾,3-dien-7-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:

1,5-quinide (665-27-0) → (1R,8R,10R,11R)-3-{5-[6-Bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-6-methoxy-pyrazin-2-yl}-10-hydroxy-8-methoxy-11-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5-aza-tricyclo[6.3.1.02,6]dodeca-2(6),3-dien-7-one (756894-02-7)

Guidance literature:

Multi-step reaction with 16 steps

1: triethylamine; DMAP / dimethylformamide / 23 °C

2: pyridinium dichromate; Celite; molecular sieves 4 Angstroem / acetonitrile / 45 °C

3: t-BuOK / tetrahydrofuran / 65 °C

4: 74 percent / molecular sieves 4 Angstroem / 5.5 h / 23 °C

5: 98 percent / triethylamine; DMAP / CH₂Cl₂ / 0.17 h / 23 °C

6: 89 percent / Pd(P(t-Bu)3)2; N-methylmorpholine N-oxide; triethylsilane / tetrahydrofuran / 3.5 h / 70 °C

7: 99 percent / H₂ / Pd/C / methanol / 7 h / 0 °C / 760 Torr

8: 93 percent / 1,1'-carbonyldiimidazole / CH₂Cl₂ / 23 °C

9: 71 percent / tetrahydrofuran / -78 - 0 °C

10: 74 percent / Pd(OAc)2; DMSO / 2-methyl-propan-2-ol; acetic acid / 10 h / 60 °C

11: H₂ / Pd/C / ethyl acetate / 0.5 h / 23 °C

12: NaH / tetrahydrofuran / 1 h / 23 °C

13: N-bromosuccinimide / 0.25 h / 0 - 23 °C

14: n-BuLi / tetrahydrofuran / 0.25 h / -78 °C

15: 77 percent / Pd(PPh₃)4; aq. Na₂CO₃; benzene / methanol / 65 h / 50 °C

16: aq. LiBF₄ / acetonitrile / 30 h / 45 - 50 °C

With triethylsilane; dmap; palladium diacetate; N-Bromosuccinimide; dipyridinium dichromate; lithium tetrafluoroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; bis(tri-t-butylphosphine)palladium⁽⁰⁾; 4 A molecular sieve; Celite; potassium tert-butylate; hydrogen; sodium hydride; sodium carbonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; 1,1'-carbonyldiimidazole; benzene; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; acetic acid; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; 3: Wittig olefination / 10: intramolecular Heck cyclization / 15: Suzuki coupling;

DOI:10.1021/ja050586v

Reference yield:

D-(-)-quinic acid (77-95-2) → (1R,8R,10R,11R)-3-{5-[6-Bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-6-methoxy-pyrazin-2-yl}-10-hydroxy-8-methoxy-11-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5-aza-tricyclo[6.3.1.02,6]dodeca-2(6),3-dien-7-one (756894-02-7)

Guidance literature:

Multi-step reaction with 17 steps

1: Amberlyst H⁺ resin; benzene / dimethylformamide / Heating

2: triethylamine; DMAP / dimethylformamide / 23 °C

3: pyridinium dichromate; Celite; molecular sieves 4 Angstroem / acetonitrile / 45 °C

4: t-BuOK / tetrahydrofuran / 65 °C

5: 74 percent / molecular sieves 4 Angstroem / 5.5 h / 23 °C

6: 98 percent / triethylamine; DMAP / CH₂Cl₂ / 0.17 h / 23 °C

7: 89 percent / Pd(P(t-Bu)3)2; N-methylmorpholine N-oxide; triethylsilane / tetrahydrofuran / 3.5 h / 70 °C

8: 99 percent / H₂ / Pd/C / methanol / 7 h / 0 °C / 760 Torr

9: 93 percent / 1,1'-carbonyldiimidazole / CH₂Cl₂ / 23 °C

10: 71 percent / tetrahydrofuran / -78 - 0 °C

11: 74 percent / Pd(OAc)2; DMSO / 2-methyl-propan-2-ol; acetic acid / 10 h / 60 °C

12: H₂ / Pd/C / ethyl acetate / 0.5 h / 23 °C

13: NaH / tetrahydrofuran / 1 h / 23 °C

14: N-bromosuccinimide / 0.25 h / 0 - 23 °C

15: n-BuLi / tetrahydrofuran / 0.25 h / -78 °C

16: 77 percent / Pd(PPh₃)4; aq. Na₂CO₃; benzene / methanol / 65 h / 50 °C

17: aq. LiBF₄ / acetonitrile / 30 h / 45 - 50 °C

With triethylsilane; dmap; palladium diacetate; N-Bromosuccinimide; dipyridinium dichromate; lithium tetrafluoroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; bis(tri-t-butylphosphine)palladium⁽⁰⁾; 4 A molecular sieve; Amberlyst H⁺ resin; Celite; potassium tert-butylate; hydrogen; sodium hydride; sodium carbonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; 1,1'-carbonyldiimidazole; benzene; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; acetic acid; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; 4: Wittig olefination / 11: intramolecular Heck cyclization / 16: Suzuki coupling;

DOI:10.1021/ja050586v

Reference yield:

(1R,3R,5R)-3-[(tert-butyldimethylsilyl)oxy]-1-hydroxy-6-oxa-bicyclo[3.2.1]octane-4,7-dione (766529-94-6) → (1R,8R,10R,11R)-3-{5-[6-Bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-6-methoxy-pyrazin-2-yl}-10-hydroxy-8-methoxy-11-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5-aza-tricyclo[6.3.1.02,6]dodeca-2(6),3-dien-7-one (756894-02-7)

Guidance literature:

Multi-step reaction with 14 steps

1: t-BuOK / tetrahydrofuran / 65 °C

2: 74 percent / molecular sieves 4 Angstroem / 5.5 h / 23 °C

3: 98 percent / triethylamine; DMAP / CH₂Cl₂ / 0.17 h / 23 °C

4: 89 percent / Pd(P(t-Bu)3)2; N-methylmorpholine N-oxide; triethylsilane / tetrahydrofuran / 3.5 h / 70 °C

5: 99 percent / H₂ / Pd/C / methanol / 7 h / 0 °C / 760 Torr

6: 93 percent / 1,1'-carbonyldiimidazole / CH₂Cl₂ / 23 °C

7: 71 percent / tetrahydrofuran / -78 - 0 °C

8: 74 percent / Pd(OAc)2; DMSO / 2-methyl-propan-2-ol; acetic acid / 10 h / 60 °C

9: H₂ / Pd/C / ethyl acetate / 0.5 h / 23 °C

10: NaH / tetrahydrofuran / 1 h / 23 °C

11: N-bromosuccinimide / 0.25 h / 0 - 23 °C

12: n-BuLi / tetrahydrofuran / 0.25 h / -78 °C

13: 77 percent / Pd(PPh₃)4; aq. Na₂CO₃; benzene / methanol / 65 h / 50 °C

14: aq. LiBF₄ / acetonitrile / 30 h / 45 - 50 °C

With triethylsilane; dmap; palladium diacetate; N-Bromosuccinimide; lithium tetrafluoroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; bis(tri-t-butylphosphine)palladium⁽⁰⁾; 4 A molecular sieve; potassium tert-butylate; hydrogen; sodium hydride; sodium carbonate; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; 1,1'-carbonyldiimidazole; benzene; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; acetic acid; ethyl acetate; acetonitrile; tert-butyl alcohol; 1: Wittig olefination / 8: intramolecular Heck cyclization / 13: Suzuki coupling;

DOI:10.1021/ja050586v

upstream raw materials:

(1R,8R,10R,11R)-3-{5-[6-Bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-6-methoxy-pyrazin-2-yl}-10-(tert-butyl-dimethyl-silanyloxy)-8-methoxy-11-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5-aza-tricyclo[6.3.1.0^2,6]dodeca-2⁽⁶⁾,3-dien-7-one

(1R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-4-methyl-cyclohex-3-enecarboxylic acid methyl ester

(3R,5R)-5-[(tert-butyldimethylsilyl)oxy]-1,3-dihydroxy-4-methylene-cyclohexanecarboxylic acid methyl ester

(1R,3R,5R)-3-Acetoxy-5-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-4-methylene-cyclohexanecarboxylic acid methyl ester

Downstream raw materials:

(1R,8R,11R)-3-{5-[6-Bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-6-methoxy-pyrazin-2-yl}-8-methoxy-11-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5-aza-tricyclo[6.3.1.0^2,6]dodeca-2⁽⁶⁾,3-diene-7,10-dione

(1R,8S,9R,11R)-9-Bromo-3-{5-[6-bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-6-methoxy-pyrazin-2-yl}-8-methoxy-11-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5-aza-tricyclo[6.3.1.0^2,6]dodeca-2⁽⁶⁾,3-diene-7,10-dione

(1R,8R,11R)-3-{5-[6-Bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-6-methoxy-pyrazin-2-yl}-8-methoxy-11-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5-aza-tricyclo[6.3.1.0^2,6]dodeca-2⁽⁶⁾,3-diene-7,10-dione 10-oxime

C₄₆H₅₀BrN₅O₉S₂Si

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