(E)-(2R,3S,4S,5R,6S,7R,10S,13S,14R,15R,16S)-2,7,13-tris{[tert-butyl(dimethyl)silyl]oxy}-3-methoxy-17-[(4-methoxybenzyl)oxy]-4,6,8,10,14,16-hexamethyl-11-oxo-5,15-bis[(triethylsilyl)oxy]heptadec-8-enoic acid allyl ester

Base Information

Chemical Name:(E)-(2R,3S,4S,5R,6S,7R,10S,13S,14R,15R,16S)-2,7,13-tris{[tert-butyl(dimethyl)silyl]oxy}-3-methoxy-17-[(4-methoxybenzyl)oxy]-4,6,8,10,14,16-hexamethyl-11-oxo-5,15-bis[(triethylsilyl)oxy]heptadec-8-enoic acid allyl ester
CAS No.:857847-29-1
Molecular Formula:C₆₅H₁₂₆O₁₁Si₅
Molecular Weight:1224.14
Hs Code.:

(E)-(2R,3S,4S,5R,6S,7R,10S,13S,14R,15R,16S)-2,7,13-tris{[tert-butyl(dimethyl)silyl]oxy}-3-methoxy-17-[(4-methoxybenzyl)oxy]-4,6,8,10,14,16-hexamethyl-11-oxo-5,15-bis[(triethylsilyl)oxy]heptadec-8-enoic acid allyl ester

Synonyms:(E)-(2R,3S,4S,5R,6S,7R,10S,13S,14R,15R,16S)-2,7,13-tris{[tert-butyl(dimethyl)silyl]oxy}-3-methoxy-17-[(4-methoxybenzyl)oxy]-4,6,8,10,14,16-hexamethyl-11-oxo-5,15-bis[(triethylsilyl)oxy]heptadec-8-enoic acid allyl ester

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Chemical Property of (E)-(2R,3S,4S,5R,6S,7R,10S,13S,14R,15R,16S)-2,7,13-tris{[tert-butyl(dimethyl)silyl]oxy}-3-methoxy-17-[(4-methoxybenzyl)oxy]-4,6,8,10,14,16-hexamethyl-11-oxo-5,15-bis[(triethylsilyl)oxy]heptadec-8-enoic acid allyl ester

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Technology Process of (E)-(2R,3S,4S,5R,6S,7R,10S,13S,14R,15R,16S)-2,7,13-tris{[tert-butyl(dimethyl)silyl]oxy}-3-methoxy-17-[(4-methoxybenzyl)oxy]-4,6,8,10,14,16-hexamethyl-11-oxo-5,15-bis[(triethylsilyl)oxy]heptadec-8-enoic acid allyl ester

There total 24 articles about (E)-(2R,3S,4S,5R,6S,7R,10S,13S,14R,15R,16S)-2,7,13-tris{[tert-butyl(dimethyl)silyl]oxy}-3-methoxy-17-[(4-methoxybenzyl)oxy]-4,6,8,10,14,16-hexamethyl-11-oxo-5,15-bis[(triethylsilyl)oxy]heptadec-8-enoic acid allyl 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: 87.0%

: 857847-19-9
(E)-(2R,3S,4S,5R,6S,7R,10S,13S,14R,15R,16S)-2,7-bis{[tert-butyl(dimethyl)silyl]oxy}-13-hydroxy-3-methoxy-17-[(4-methoxybenzyl)oxy]-4,6,8,10,14,16-hexamethyl-11-oxo-5,15-bis[(triethylsilyl)oxy]heptadec-8-enoic acid allyl ester

: 69739-34-0
t-butyldimethylsiyl triflate

: 857847-29-1
(E)-(2R,3S,4S,5R,6S,7R,10S,13S,14R,15R,16S)-2,7,13-tris{[tert-butyl(dimethyl)silyl]oxy}-3-methoxy-17-[(4-methoxybenzyl)oxy]-4,6,8,10,14,16-hexamethyl-11-oxo-5,15-bis[(triethylsilyl)oxy]heptadec-8-enoic acid allyl ester

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 0.5h;
DOI:10.1055/s-2005-865302

Reference yield:

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

: 857847-29-1
(E)-(2R,3S,4S,5R,6S,7R,10S,13S,14R,15R,16S)-2,7,13-tris{[tert-butyl(dimethyl)silyl]oxy}-3-methoxy-17-[(4-methoxybenzyl)oxy]-4,6,8,10,14,16-hexamethyl-11-oxo-5,15-bis[(triethylsilyl)oxy]heptadec-8-enoic acid allyl ester

Guidance literature:: Multi-step reaction with 18 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

13.1: 82 percent / proton sponge / CH₂Cl₂ / 24 h / 0 °C

14.1: bis[(dibutyl)chlorotin]oxide / 96 h / 160 °C

15.1: aq. DDQ / CH₂Cl₂ / 1 h / pH 7

16.1: 187 mg / N-methylmorpholine N-oxide; TPAP; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.25 h

17.1: KHMDS; 4 Angstroem molecular sieves / tetrahydrofuran; toluene / -78 °C

17.2: 59 percent / tetrahydrofuran; toluene / 0.08 h / -78 °C

18.1: 87 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; manganese(IV) oxide; AD-mix-α; tetrapropylammonium perruthennate; Proton Sponge; methanesulfonamide; 4 A molecular sieve; tris(pentafluorophenyl)borate; trimethylaluminum; potassium hexamethylsilazane; diisobutylaluminium hydride; 1,3-dichlorotetrabutyldistannoxane; ozone; 4-methylmorpholine N-oxide; isopropyl alcohol; 1-[{4-(phenylazo)-phenyl}-azo]-2-naphthalenol; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; ethanol; hexane; n-heptane; dichloromethane; N,N-dimethyl-formamide; toluene; 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:

: 857847-03-1
(2R,3S)-3-(4-Methoxy-benzyloxy)-2-methyl-butyraldehyde

: 857847-29-1
(E)-(2R,3S,4S,5R,6S,7R,10S,13S,14R,15R,16S)-2,7,13-tris{[tert-butyl(dimethyl)silyl]oxy}-3-methoxy-17-[(4-methoxybenzyl)oxy]-4,6,8,10,14,16-hexamethyl-11-oxo-5,15-bis[(triethylsilyl)oxy]heptadec-8-enoic acid allyl ester

Guidance literature:: Multi-step reaction with 17 steps

1.1: 209 mg / CH₂Cl₂; ethanol / 15 h / 20 °C

2.1: 91 percent / DIBAL-H / CH₂Cl₂; hexane / 1 h / -78 °C

3.1: 97 percent / MnO₂ / CH₂Cl₂ / 1 h / 20 °C

4.1: 3.36 g / CH₂Cl₂ / 1.33 h / -78 - 0 °C

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

5.2: 89 percent / CH₂Cl₂ / -20 - 20 °C

6.1: 1.95 g / 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

7.1: 88 percent / DIBAL-H / heptane; tetrahydrofuran / 0.25 h / -78 °C

8.1: 91 percent / tris(pentafluorophenyl)borane monohydrate; i-PrOH / diethyl ether / 0.5 h / -78 - -50 °C

9.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0.25 h / 0 °C

10.1: 87 percent / aq. AD-mix α; methanesulfonamide / 2-methyl-propan-2-ol / 120 h / 0 °C

11.1: 99 percent / imidazole / dimethylformamide / 16 h / 0 °C

12.1: 82 percent / proton sponge / CH₂Cl₂ / 24 h / 0 °C

13.1: bis[(dibutyl)chlorotin]oxide / 96 h / 160 °C

14.1: aq. DDQ / CH₂Cl₂ / 1 h / pH 7

15.1: 187 mg / N-methylmorpholine N-oxide; TPAP; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.25 h

16.1: KHMDS; 4 Angstroem molecular sieves / tetrahydrofuran; toluene / -78 °C

16.2: 59 percent / tetrahydrofuran; toluene / 0.08 h / -78 °C

17.1: 87 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; manganese(IV) oxide; AD-mix-α; tetrapropylammonium perruthennate; Proton Sponge; methanesulfonamide; 4 A molecular sieve; tris(pentafluorophenyl)borate; trimethylaluminum; potassium hexamethylsilazane; diisobutylaluminium hydride; 1,3-dichlorotetrabutyldistannoxane; 4-methylmorpholine N-oxide; isopropyl alcohol; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; ethanol; hexane; n-heptane; dichloromethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 1.1: Wittig reaction / 8.1: vinylogous Mukaiyama aldol reaction / 10.1: Sharpless asymmetric dihydroxylation;
DOI:10.1055/s-2005-865302