(1'S,1''R,2''R,3S,4S,6S,8R,10S)-3-(tert-butyldimethylsilyloxy)-11-hydroxy-4,6,8,10-tetramethylundecanoic acid 6''-bromo-6''-cyano-1-[2'''-(4'''-methoxymenzyloxymethyl)cyclopentyl]hexa-3''E,5''E-dienyl ester

Base Information

Chemical Name:(1'S,1''R,2''R,3S,4S,6S,8R,10S)-3-(tert-butyldimethylsilyloxy)-11-hydroxy-4,6,8,10-tetramethylundecanoic acid 6''-bromo-6''-cyano-1-[2'''-(4'''-methoxymenzyloxymethyl)cyclopentyl]hexa-3''E,5''E-dienyl ester
CAS No.:714974-19-3
Molecular Formula:C₄₂H₆₈BrNO₆Si
Molecular Weight:790.995
Hs Code.:

(1'S,1''R,2''R,3S,4S,6S,8R,10S)-3-(tert-butyldimethylsilyloxy)-11-hydroxy-4,6,8,10-tetramethylundecanoic acid 6''-bromo-6''-cyano-1-[2'''-(4'''-methoxymenzyloxymethyl)cyclopentyl]hexa-3''E,5''E-dienyl ester

Synonyms:(1'S,1''R,2''R,3S,4S,6S,8R,10S)-3-(tert-butyldimethylsilyloxy)-11-hydroxy-4,6,8,10-tetramethylundecanoic acid 6''-bromo-6''-cyano-1-[2'''-(4'''-methoxymenzyloxymethyl)cyclopentyl]hexa-3''E,5''E-dienyl ester

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Chemical Property of (1'S,1''R,2''R,3S,4S,6S,8R,10S)-3-(tert-butyldimethylsilyloxy)-11-hydroxy-4,6,8,10-tetramethylundecanoic acid 6''-bromo-6''-cyano-1-[2'''-(4'''-methoxymenzyloxymethyl)cyclopentyl]hexa-3''E,5''E-dienyl ester

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Technology Process of (1'S,1''R,2''R,3S,4S,6S,8R,10S)-3-(tert-butyldimethylsilyloxy)-11-hydroxy-4,6,8,10-tetramethylundecanoic acid 6''-bromo-6''-cyano-1-[2'''-(4'''-methoxymenzyloxymethyl)cyclopentyl]hexa-3''E,5''E-dienyl ester

There total 32 articles about (1'S,1''R,2''R,3S,4S,6S,8R,10S)-3-(tert-butyldimethylsilyloxy)-11-hydroxy-4,6,8,10-tetramethylundecanoic acid 6''-bromo-6''-cyano-1-[2'''-(4'''-methoxymenzyloxymethyl)cyclopentyl]hexa-3''E,5''E-dienyl 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: 93.0%

: 714974-18-2
(1''S,1'''R,2'''R,3S,4S,6S,8R,10S)-3-(tert-butyldimethyl-silyloxy)-4,6,8,10-tetramethyl-11-(tetrahydropyran-2'-yloxy)undecanoic acid 6''-bromo-6''-cyano-1-[2'''-(4'''-methoxymenzyloxymethyl)cyclopentyl]hexa-3''E,5''E-dienyl ester

: 714974-19-3
(1'S,1''R,2''R,3S,4S,6S,8R,10S)-3-(tert-butyldimethylsilyloxy)-11-hydroxy-4,6,8,10-tetramethylundecanoic acid 6''-bromo-6''-cyano-1-[2'''-(4'''-methoxymenzyloxymethyl)cyclopentyl]hexa-3''E,5''E-dienyl ester

Guidance literature:: With pyridinium p-toluenesulfonate; In ethanol; at 50 ℃; for 10h;
DOI:10.1021/ol049356w DOI:10.1021/jo062089i

Reference yield:

: 90270-02-3,97937-36-5
(2R,4S)-1-hydroxy-2,4-dimethylpentyl acetate

: 714974-19-3
(1'S,1''R,2''R,3S,4S,6S,8R,10S)-3-(tert-butyldimethylsilyloxy)-11-hydroxy-4,6,8,10-tetramethylundecanoic acid 6''-bromo-6''-cyano-1-[2'''-(4'''-methoxymenzyloxymethyl)cyclopentyl]hexa-3''E,5''E-dienyl ester

Guidance literature:: Multi-step reaction with 19 steps

1.1: 98 percent / imidazole / CH₂Cl₂ / 0.5 h / 20 °C

2.1: 98 percent / K₂CO₃; MeOH / 2 h / 20 °C

3.1: imidazole / dimethylformamide / 0 - 20 °C

4.1: 4.19 g / PPTS; EtOH / 7 h / 50 °C

5.1: 88 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH₂Cl₂ / 0.5 h / 20 °C

6.1: n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C

6.2: tetrahydrofuran; hexane / 1 h / -30 °C

6.3: tetrahydrofuran; hexane / -20 °C

7.1: 2.44 g / Bu₃P; HCO₂NH₄ / Pd(PPh₃)4 / toluene / 1 h / 70 °C

8.1: 97 percent / DDQ; H₂O / CH₂Cl₂ / 0.5 h / 20 °C

9.1: 80 percent / TiCl₄ / CH₂Cl₂; hexane / 0.25 h / -15 °C

10.1: 91 percent / H₂ / Rh[(nbd)dppb]BF₄ / CH₂Cl₂ / 2 h / 20 °C / 7500.75 Torr

11.1: 100 percent / PPTS / CH₂Cl₂ / 2 h / 20 °C

12.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C

13.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH₂Cl₂ / 0.5 h / 20 °C

14.1: 92 percent / SmI₂ / tetrahydrofuran / 0.33 h / -78 °C

15.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

16.1: 347 mg / LiOH; aq. H₂O₂ / tetrahydrofuran / 3 h / 0 °C

17.1: Et₃N / benzene / 1 h / 20 °C

18.1: 204 mg / Et₃N; DMAP / benzene / 0.5 h / 20 °C

19.1: 93 percent / PPTS / ethanol / 10 h / 50 °C

With 1H-imidazole; 2,6-dimethylpyridine; methanol; dmap; lithium hydroxide; n-butyllithium; N-methyl-2-indolinone; samarium diiodide; tetrapropylammonium perruthennate; ethanol; tributylphosphine; 4 A molecular sieve; tetrabutyl ammonium fluoride; water; hydrogen; dihydrogen peroxide; ammonium formate; pyridinium p-toluenesulfonate; titanium tetrachloride; potassium carbonate; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tetrakis(triphenylphosphine) palladium⁽⁰⁾; {(1,4-bis(diphenylphosphino)butane)Rh(norbornadiene)}BF₄; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1021/jo062089i

Reference yield:

: 147782-80-7
(2S,4R)-5-(tert-butyl(dimethyl)silyloxy)-2,4-dimethyl-1-pentanol

: 714974-19-3
(1'S,1''R,2''R,3S,4S,6S,8R,10S)-3-(tert-butyldimethylsilyloxy)-11-hydroxy-4,6,8,10-tetramethylundecanoic acid 6''-bromo-6''-cyano-1-[2'''-(4'''-methoxymenzyloxymethyl)cyclopentyl]hexa-3''E,5''E-dienyl ester

Guidance literature:: Multi-step reaction with 17 steps

1.1: imidazole / dimethylformamide / 0 - 20 °C

2.1: 4.19 g / PPTS; EtOH / 7 h / 50 °C

3.1: 88 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH₂Cl₂ / 0.5 h / 20 °C

4.1: n-BuLi / tetrahydrofuran; hexane / -78 - -40 °C

4.2: tetrahydrofuran; hexane / 1 h / -30 °C

4.3: tetrahydrofuran; hexane / -20 °C

5.1: 2.44 g / Bu₃P; HCO₂NH₄ / Pd(PPh₃)4 / toluene / 1 h / 70 °C

6.1: 97 percent / DDQ; H₂O / CH₂Cl₂ / 0.5 h / 20 °C

7.1: 80 percent / TiCl₄ / CH₂Cl₂; hexane / 0.25 h / -15 °C

8.1: 91 percent / H₂ / Rh[(nbd)dppb]BF₄ / CH₂Cl₂ / 2 h / 20 °C / 7500.75 Torr

9.1: 100 percent / PPTS / CH₂Cl₂ / 2 h / 20 °C

10.1: 96 percent / TBAF / tetrahydrofuran / 3 h / 0 °C

11.1: 89 percent / TPAP; 4 Angstroem molecular sieves; NMO / CH₂Cl₂ / 0.5 h / 20 °C

12.1: 92 percent / SmI₂ / tetrahydrofuran / 0.33 h / -78 °C

13.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

14.1: 347 mg / LiOH; aq. H₂O₂ / tetrahydrofuran / 3 h / 0 °C

15.1: Et₃N / benzene / 1 h / 20 °C

16.1: 204 mg / Et₃N; DMAP / benzene / 0.5 h / 20 °C

17.1: 93 percent / PPTS / ethanol / 10 h / 50 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; lithium hydroxide; n-butyllithium; N-methyl-2-indolinone; samarium diiodide; tetrapropylammonium perruthennate; ethanol; tributylphosphine; 4 A molecular sieve; tetrabutyl ammonium fluoride; water; hydrogen; dihydrogen peroxide; ammonium formate; pyridinium p-toluenesulfonate; titanium tetrachloride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tetrakis(triphenylphosphine) palladium⁽⁰⁾; {(1,4-bis(diphenylphosphino)butane)Rh(norbornadiene)}BF₄; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1021/jo062089i