(E)-(2R,3S,4S,5R,6S,7R,10S,11S)-2,7-bis{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-11-[(4-methoxybenzyl)oxy]-4,6,8,10-tetramethyl-5-[(triethylsilyl)oxy]dodec-8-enoic acid methyl ester

Base Information

Chemical Name:(E)-(2R,3S,4S,5R,6S,7R,10S,11S)-2,7-bis{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-11-[(4-methoxybenzyl)oxy]-4,6,8,10-tetramethyl-5-[(triethylsilyl)oxy]dodec-8-enoic acid methyl ester
CAS No.:857847-23-5
Molecular Formula:C₄₃H₈₂O₈Si₃
Molecular Weight:811.376
Hs Code.:

(E)-(2R,3S,4S,5R,6S,7R,10S,11S)-2,7-bis{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-11-[(4-methoxybenzyl)oxy]-4,6,8,10-tetramethyl-5-[(triethylsilyl)oxy]dodec-8-enoic acid methyl ester

Synonyms:(E)-(2R,3S,4S,5R,6S,7R,10S,11S)-2,7-bis{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-11-[(4-methoxybenzyl)oxy]-4,6,8,10-tetramethyl-5-[(triethylsilyl)oxy]dodec-8-enoic acid methyl ester

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Chemical Property of (E)-(2R,3S,4S,5R,6S,7R,10S,11S)-2,7-bis{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-11-[(4-methoxybenzyl)oxy]-4,6,8,10-tetramethyl-5-[(triethylsilyl)oxy]dodec-8-enoic acid methyl ester

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Technology Process of (E)-(2R,3S,4S,5R,6S,7R,10S,11S)-2,7-bis{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-11-[(4-methoxybenzyl)oxy]-4,6,8,10-tetramethyl-5-[(triethylsilyl)oxy]dodec-8-enoic acid methyl ester

There total 15 articles about (E)-(2R,3S,4S,5R,6S,7R,10S,11S)-2,7-bis{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-11-[(4-methoxybenzyl)oxy]-4,6,8,10-tetramethyl-5-[(triethylsilyl)oxy]dodec-8-enoic acid methyl 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: 99.0%

: 857847-09-7
(E)-(2R,3S,4S,5R,6S,7R,10S,11S)-7-{[tert-butyl(dimethyl)silyl]oxy}-2,3-dihydroxy-11-[(4-methoxybenzyl)oxy]-4,6,8,10-tetramethyl-5-[(triethylsilyl)oxy]dodec-8-enoic acid methyl ester

: 18162-48-6
tert-butyldimethylsilyl chloride

: 857847-23-5
(E)-(2R,3S,4S,5R,6S,7R,10S,11S)-2,7-bis{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-11-[(4-methoxybenzyl)oxy]-4,6,8,10-tetramethyl-5-[(triethylsilyl)oxy]dodec-8-enoic acid methyl ester

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 0 ℃; for 16h;
DOI:10.1055/s-2005-865302

Reference yield:

: 857847-01-9
1-((1S,2S)-1,2-Dimethyl-but-3-enyloxymethyl)-4-methoxy-benzene

: 857847-23-5
(E)-(2R,3S,4S,5R,6S,7R,10S,11S)-2,7-bis{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-11-[(4-methoxybenzyl)oxy]-4,6,8,10-tetramethyl-5-[(triethylsilyl)oxy]dodec-8-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 12 steps

1.1: O₃; Sudan Red III / ethanol; CH₂Cl₂ / 0.17 h / -78 °C

1.2: PPh₃ / ethanol; CH₂Cl₂ / 1 h / -78 °C

2.1: 209 mg / CH₂Cl₂; ethanol / 15 h / 20 °C

3.1: 91 percent / DIBAL-H / CH₂Cl₂; hexane / 1 h / -78 °C

4.1: 97 percent / MnO₂ / CH₂Cl₂ / 1 h / 20 °C

5.1: 3.36 g / CH₂Cl₂ / 1.33 h / -78 - 0 °C

6.1: Me₃Al / CH₂Cl₂; heptane / 1 h / 20 °C

6.2: 89 percent / CH₂Cl₂ / -20 - 20 °C

7.1: 1.95 g / 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

8.1: 88 percent / DIBAL-H / heptane; tetrahydrofuran / 0.25 h / -78 °C

9.1: 91 percent / tris(pentafluorophenyl)borane monohydrate; i-PrOH / diethyl ether / 0.5 h / -78 - -50 °C

10.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / 0 °C

11.1: 87 percent / aq. AD-mix α; methanesulfonamide / 2-methyl-propan-2-ol / 120 h / 0 °C

12.1: 99 percent / imidazole / dimethylformamide / 16 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; manganese(IV) oxide; AD-mix-α; methanesulfonamide; tris(pentafluorophenyl)borate; trimethylaluminum; diisobutylaluminium hydride; ozone; isopropyl alcohol; 1-[{4-(phenylazo)-phenyl}-azo]-2-naphthalenol; In tetrahydrofuran; diethyl ether; ethanol; hexane; n-heptane; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; 2.1: Wittig reaction / 9.1: vinylogous Mukaiyama aldol reaction / 11.1: Sharpless asymmetric dihydroxylation;
DOI:10.1055/s-2005-865302

Reference yield:

: 824-94-2
p-methoxybenzyl chloride

: 857847-23-5
(E)-(2R,3S,4S,5R,6S,7R,10S,11S)-2,7-bis{[tert-butyl(dimethyl)silyl]oxy}-3-hydroxy-11-[(4-methoxybenzyl)oxy]-4,6,8,10-tetramethyl-5-[(triethylsilyl)oxy]dodec-8-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 13 steps

1.1: O₃; Sudan Red III / ethanol; CH₂Cl₂ / 0.17 h / -78 °C

1.2: PPh₃ / ethanol; CH₂Cl₂ / 1 h / -78 °C

2.1: 209 mg / CH₂Cl₂; ethanol / 15 h / 20 °C

3.1: 91 percent / DIBAL-H / CH₂Cl₂; hexane / 1 h / -78 °C

4.1: 97 percent / MnO₂ / CH₂Cl₂ / 1 h / 20 °C

5.1: 3.36 g / CH₂Cl₂ / 1.33 h / -78 - 0 °C

6.1: Me₃Al / CH₂Cl₂; heptane / 1 h / 20 °C

6.2: 89 percent / CH₂Cl₂ / -20 - 20 °C

7.1: 1.95 g / 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

8.1: 88 percent / DIBAL-H / heptane; tetrahydrofuran / 0.25 h / -78 °C

9.1: 91 percent / tris(pentafluorophenyl)borane monohydrate; i-PrOH / diethyl ether / 0.5 h / -78 - -50 °C

10.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / 0 °C

11.1: 87 percent / aq. AD-mix α; methanesulfonamide / 2-methyl-propan-2-ol / 120 h / 0 °C

12.1: 99 percent / imidazole / dimethylformamide / 16 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; manganese(IV) oxide; AD-mix-α; methanesulfonamide; tris(pentafluorophenyl)borate; trimethylaluminum; diisobutylaluminium hydride; ozone; isopropyl alcohol; 1-[{4-(phenylazo)-phenyl}-azo]-2-naphthalenol; In tetrahydrofuran; diethyl ether; ethanol; hexane; n-heptane; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; 3.1: Wittig reaction / 10.1: vinylogous Mukaiyama aldol reaction / 12.1: Sharpless asymmetric dihydroxylation;
DOI:10.1055/s-2005-865302