(2E,4E)-(6S,7R,8S,9S,10S,11R)-10-(tert-Butyl-dimethyl-silanyloxy)-8-((Z)-3-iodo-2-methyl-allyl)-12-(4-methoxy-benzyloxy)-2,4,6,9,11-pentamethyl-7-triethylsilanyloxy-dodeca-2,4-dienoic acid ethyl ester

Base Information

Chemical Name:(2E,4E)-(6S,7R,8S,9S,10S,11R)-10-(tert-Butyl-dimethyl-silanyloxy)-8-((Z)-3-iodo-2-methyl-allyl)-12-(4-methoxy-benzyloxy)-2,4,6,9,11-pentamethyl-7-triethylsilanyloxy-dodeca-2,4-dienoic acid ethyl ester
CAS No.:412342-87-1
Molecular Formula:C₄₃H₇₅IO₆Si₂
Molecular Weight:871.14
Hs Code.:

(2E,4E)-(6S,7R,8S,9S,10S,11R)-10-(tert-Butyl-dimethyl-silanyloxy)-8-((Z)-3-iodo-2-methyl-allyl)-12-(4-methoxy-benzyloxy)-2,4,6,9,11-pentamethyl-7-triethylsilanyloxy-dodeca-2,4-dienoic acid ethyl ester

Synonyms:(2E,4E)-(6S,7R,8S,9S,10S,11R)-10-(tert-Butyl-dimethyl-silanyloxy)-8-((Z)-3-iodo-2-methyl-allyl)-12-(4-methoxy-benzyloxy)-2,4,6,9,11-pentamethyl-7-triethylsilanyloxy-dodeca-2,4-dienoic acid ethyl ester

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Chemical Property of (2E,4E)-(6S,7R,8S,9S,10S,11R)-10-(tert-Butyl-dimethyl-silanyloxy)-8-((Z)-3-iodo-2-methyl-allyl)-12-(4-methoxy-benzyloxy)-2,4,6,9,11-pentamethyl-7-triethylsilanyloxy-dodeca-2,4-dienoic acid ethyl ester

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Technology Process of (2E,4E)-(6S,7R,8S,9S,10S,11R)-10-(tert-Butyl-dimethyl-silanyloxy)-8-((Z)-3-iodo-2-methyl-allyl)-12-(4-methoxy-benzyloxy)-2,4,6,9,11-pentamethyl-7-triethylsilanyloxy-dodeca-2,4-dienoic acid ethyl ester

There total 20 articles about (2E,4E)-(6S,7R,8S,9S,10S,11R)-10-(tert-Butyl-dimethyl-silanyloxy)-8-((Z)-3-iodo-2-methyl-allyl)-12-(4-methoxy-benzyloxy)-2,4,6,9,11-pentamethyl-7-triethylsilanyloxy-dodeca-2,4-dienoic acid ethyl 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: 97.0%

: 21382-82-1
(carbethoxyethylidene)triphenylphosphorane

: 412342-86-0
(E)-(4S,5R,6S,7S,8S,9R)-8-(tert-Butyl-dimethyl-silanyloxy)-6-((Z)-3-iodo-2-methyl-allyl)-10-(4-methoxy-benzyloxy)-2,4,7,9-tetramethyl-5-triethylsilanyloxy-dec-2-enal

: 412342-87-1
(2E,4E)-(6S,7R,8S,9S,10S,11R)-10-(tert-Butyl-dimethyl-silanyloxy)-8-((Z)-3-iodo-2-methyl-allyl)-12-(4-methoxy-benzyloxy)-2,4,6,9,11-pentamethyl-7-triethylsilanyloxy-dodeca-2,4-dienoic acid ethyl ester

Guidance literature:: In toluene; for 16h; Heating;
DOI:10.1021/ol017266a

Reference yield:

: (2R,3S,4S)-1-(tert-Butyl-diphenyl-silanyloxy)-2,4-dimethyl-hex-5-en-3-ol

: 412342-87-1
(2E,4E)-(6S,7R,8S,9S,10S,11R)-10-(tert-Butyl-dimethyl-silanyloxy)-8-((Z)-3-iodo-2-methyl-allyl)-12-(4-methoxy-benzyloxy)-2,4,6,9,11-pentamethyl-7-triethylsilanyloxy-dodeca-2,4-dienoic acid ethyl ester

Guidance literature:: Multi-step reaction with 20 steps

1.1: 92 percent / TfOH / CH₂Cl₂ / 3.5 h / 20 °C

2.1: catecholborane / (Ph₃P)3RhCl / tetrahydrofuran / 0 - 20 °C

2.2: 27.5percent H₂O₂; 2N NaOH / methanol / 2 h / 0 °C

3.1: PDC / dimethylformamide / 48 h / 20 °C

4.1: 73 percent / H₂ / 20percent Pd(OH)2/C / methanol

5.1: Li(Pr-i)2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / -78 °C

5.2: 86 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / -78 °C

6.1: aq. HF / tetrahydrofuran; acetonitrile / 20 °C

7.1: PPTS / CH₂Cl₂ / 7 h / 20 °C

8.1: LiBH₄ / tetrahydrofuran; methanol / 3 h / Heating

9.1: imidazole / dimethylformamide / 1.5 h / 0 °C

10.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -50 °C

11.1: aq. HF / tetrahydrofuran; acetonitrile / 1.5 h / 20 °C

12.1: TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.67 h / 20 °C

13.1: (n-Bu)2BOTf; Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

13.2: CH₂Cl₂ / -78 - 20 °C

14.1: 2,6-lutidine / CH₂Cl₂ / 0.75 h / -50 - 20 °C

15.1: 82 percent / LiBH₄ / diethyl ether; H₂O / 1.5 h / 20 °C

16.1: 81 percent / TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 1.17 h / 20 °C

17.1: 90 percent / toluene / 5 h / Heating

18.1: 87 percent / i-Bu₂AlH / toluene / 0.5 h / -78 °C

19.1: 98 percent / MnO₂ / CHCl₃ / 6 h / Heating

20.1: 97 percent / toluene / 16 h / Heating

With 1H-imidazole; 2,6-dimethylpyridine; manganese(IV) oxide; dipyridinium dichromate; lithium borohydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; trifluorormethanesulfonic acid; 4 A molecular sieve; Li(Pr-i)2; di-n-butylboryl trifluoromethanesulfonate; hydrogen fluoride; hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; triethylamine; benzo[1,3,2]dioxaborole; Wilkinson's catalyst; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene; acetonitrile; 13.2: Evans aldol addition / 17.1: Wittig reaction / 20.1: Wittig reaction;
DOI:10.1021/ol017266a

Reference yield:

: 412342-77-9
((2R,3S,4S)-3-Benzyloxy-2,4-dimethyl-hex-5-enyloxy)-tert-butyl-diphenyl-silane

: 412342-87-1
(2E,4E)-(6S,7R,8S,9S,10S,11R)-10-(tert-Butyl-dimethyl-silanyloxy)-8-((Z)-3-iodo-2-methyl-allyl)-12-(4-methoxy-benzyloxy)-2,4,6,9,11-pentamethyl-7-triethylsilanyloxy-dodeca-2,4-dienoic acid ethyl ester

Guidance literature:: Multi-step reaction with 19 steps

1.1: catecholborane / (Ph₃P)3RhCl / tetrahydrofuran / 0 - 20 °C

1.2: 27.5percent H₂O₂; 2N NaOH / methanol / 2 h / 0 °C

2.1: PDC / dimethylformamide / 48 h / 20 °C

3.1: 73 percent / H₂ / 20percent Pd(OH)2/C / methanol

4.1: Li(Pr-i)2 / tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / -78 °C

4.2: 86 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 2 h / -78 °C

5.1: aq. HF / tetrahydrofuran; acetonitrile / 20 °C

6.1: PPTS / CH₂Cl₂ / 7 h / 20 °C

7.1: LiBH₄ / tetrahydrofuran; methanol / 3 h / Heating

8.1: imidazole / dimethylformamide / 1.5 h / 0 °C

9.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -50 °C

10.1: aq. HF / tetrahydrofuran; acetonitrile / 1.5 h / 20 °C

11.1: TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.67 h / 20 °C

12.1: (n-Bu)2BOTf; Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

12.2: CH₂Cl₂ / -78 - 20 °C

13.1: 2,6-lutidine / CH₂Cl₂ / 0.75 h / -50 - 20 °C

14.1: 82 percent / LiBH₄ / diethyl ether; H₂O / 1.5 h / 20 °C

15.1: 81 percent / TPAP; NMO; 4 Angstroem molecular sieves / CH₂Cl₂ / 1.17 h / 20 °C

16.1: 90 percent / toluene / 5 h / Heating

17.1: 87 percent / i-Bu₂AlH / toluene / 0.5 h / -78 °C

18.1: 98 percent / MnO₂ / CHCl₃ / 6 h / Heating

19.1: 97 percent / toluene / 16 h / Heating

With 1H-imidazole; 2,6-dimethylpyridine; manganese(IV) oxide; dipyridinium dichromate; lithium borohydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; 4 A molecular sieve; Li(Pr-i)2; di-n-butylboryl trifluoromethanesulfonate; hydrogen fluoride; hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; triethylamine; benzo[1,3,2]dioxaborole; Wilkinson's catalyst; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; chloroform; water; N,N-dimethyl-formamide; toluene; acetonitrile; 12.2: Evans aldol addition / 16.1: Wittig reaction / 19.1: Wittig reaction;
DOI:10.1021/ol017266a