(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-enal

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-enal
CAS No.:857847-33-7
Molecular Formula:C₆₂H₁₂₂O₁₀Si₅
Molecular Weight:1168.07
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-enal

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-enal

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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-enal

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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-enal

There total 25 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-enal 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: 70.0%

: (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-5,15-bis[(triethylsilyl)oxy]heptadec-8-ene-1,11-diol

: 857847-33-7
(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-enal

Guidance literature:: With tetrapropylammonium perruthennate; 3 A molecular sieve; 4-methylmorpholine N-oxide; In dichloromethane; at 20 ℃; for 4h;
DOI:10.1055/s-2005-865302

Reference yield:

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

: 857847-33-7
(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-enal

Guidance literature:: Multi-step reaction with 19 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: 96 percent / aq. DDQ / CH₂Cl₂ / 1.5 h / 0 °C / pH 7

15.1: 99 percent / 3 Angstroem molecular sieves; N-methylmorpholine N-oxide; TPAP / CH₂Cl₂ / 4 h / 20 °C

16.1: 3 Angstroem molecular sieves; NaHMDS / tetrahydrofuran / -78 °C

16.2: 61 percent / tetrahydrofuran / 0.02 h / -78 °C

17.1: 87 percent / 2,6-lutidine / CH₂Cl₂ / 0.75 h / 0 °C

18.1: 61 percent / DIBAL-H / CH₂Cl₂; heptane / 1.5 h / -78 °C

19.1: 70 percent / 3 Angstroem molecular sieves; N-methylmorpholine N-oxide; TPAP / CH₂Cl₂ / 4 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; manganese(IV) oxide; AD-mix-α; tetrapropylammonium perruthennate; Proton Sponge; methanesulfonamide; 3 A molecular sieve; tris(pentafluorophenyl)borate; trimethylaluminum; sodium hexamethyldisilazane; diisobutylaluminium hydride; 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; 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

: 857847-33-7
(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-enal

Guidance literature:: Multi-step reaction with 18 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: 96 percent / aq. DDQ / CH₂Cl₂ / 1.5 h / 0 °C / pH 7

14.1: 99 percent / 3 Angstroem molecular sieves; N-methylmorpholine N-oxide; TPAP / CH₂Cl₂ / 4 h / 20 °C

15.1: 3 Angstroem molecular sieves; NaHMDS / tetrahydrofuran / -78 °C

15.2: 61 percent / tetrahydrofuran / 0.02 h / -78 °C

16.1: 87 percent / 2,6-lutidine / CH₂Cl₂ / 0.75 h / 0 °C

17.1: 61 percent / DIBAL-H / CH₂Cl₂; heptane / 1.5 h / -78 °C

18.1: 70 percent / 3 Angstroem molecular sieves; N-methylmorpholine N-oxide; TPAP / CH₂Cl₂ / 4 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; manganese(IV) oxide; AD-mix-α; tetrapropylammonium perruthennate; Proton Sponge; methanesulfonamide; 3 A molecular sieve; tris(pentafluorophenyl)borate; trimethylaluminum; sodium hexamethyldisilazane; diisobutylaluminium hydride; 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; tert-butyl alcohol; 1.1: Wittig reaction / 8.1: vinylogous Mukaiyama aldol reaction / 10.1: Sharpless asymmetric dihydroxylation;
DOI:10.1055/s-2005-865302