2''-[(E)-(4R,5S,6R,8R,9S,13R,14R,15R)-14-(tert-Butyl-dimethyl-silanyloxy)-17-(tert-butyl-diphenyl-silanyloxy)-4,8-dimethoxy-6-methoxymethoxy-5,9,13,15-tetramethyl-12-oxo-heptadec-1-enyl]-[2,4';2',4'']teroxazole-4-carbaldehyde

Base Information

Chemical Name:2''-[(E)-(4R,5S,6R,8R,9S,13R,14R,15R)-14-(tert-Butyl-dimethyl-silanyloxy)-17-(tert-butyl-diphenyl-silanyloxy)-4,8-dimethoxy-6-methoxymethoxy-5,9,13,15-tetramethyl-12-oxo-heptadec-1-enyl]-[2,4';2',4'']teroxazole-4-carbaldehyde
CAS No.:203520-18-7
Molecular Formula:C₅₇H₈₃N₃O₁₁Si₂
Molecular Weight:1042.47
Hs Code.:

2''-[(E)-(4R,5S,6R,8R,9S,13R,14R,15R)-14-(tert-Butyl-dimethyl-silanyloxy)-17-(tert-butyl-diphenyl-silanyloxy)-4,8-dimethoxy-6-methoxymethoxy-5,9,13,15-tetramethyl-12-oxo-heptadec-1-enyl]-[2,4';2',4'']teroxazole-4-carbaldehyde

Synonyms:2''-[(E)-(4R,5S,6R,8R,9S,13R,14R,15R)-14-(tert-Butyl-dimethyl-silanyloxy)-17-(tert-butyl-diphenyl-silanyloxy)-4,8-dimethoxy-6-methoxymethoxy-5,9,13,15-tetramethyl-12-oxo-heptadec-1-enyl]-[2,4';2',4'']teroxazole-4-carbaldehyde

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Chemical Property of 2''-[(E)-(4R,5S,6R,8R,9S,13R,14R,15R)-14-(tert-Butyl-dimethyl-silanyloxy)-17-(tert-butyl-diphenyl-silanyloxy)-4,8-dimethoxy-6-methoxymethoxy-5,9,13,15-tetramethyl-12-oxo-heptadec-1-enyl]-[2,4';2',4'']teroxazole-4-carbaldehyde

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Technology Process of 2''-[(E)-(4R,5S,6R,8R,9S,13R,14R,15R)-14-(tert-Butyl-dimethyl-silanyloxy)-17-(tert-butyl-diphenyl-silanyloxy)-4,8-dimethoxy-6-methoxymethoxy-5,9,13,15-tetramethyl-12-oxo-heptadec-1-enyl]-[2,4';2',4'']teroxazole-4-carbaldehyde

There total 39 articles about 2''-[(E)-(4R,5S,6R,8R,9S,13R,14R,15R)-14-(tert-Butyl-dimethyl-silanyloxy)-17-(tert-butyl-diphenyl-silanyloxy)-4,8-dimethoxy-6-methoxymethoxy-5,9,13,15-tetramethyl-12-oxo-heptadec-1-enyl]-[2,4';2',4'']teroxazole-4-carbaldehyde 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: 98.0%

: 203520-17-6
(E)-(3R,4R,5S,9S,10R,12R,13S,14R)-4-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-diphenyl-silanyloxy)-17-(4-hydroxymethyl-[2,4';2',4'']teroxazol-2''-yl)-10,14-dimethoxy-12-methoxymethoxy-3,5,9,13-tetramethyl-heptadec-16-en-6-ol

: 203520-18-7
2''-[(E)-(4R,5S,6R,8R,9S,13R,14R,15R)-14-(tert-Butyl-dimethyl-silanyloxy)-17-(tert-butyl-diphenyl-silanyloxy)-4,8-dimethoxy-6-methoxymethoxy-5,9,13,15-tetramethyl-12-oxo-heptadec-1-enyl]-[2,4';2',4'']teroxazole-4-carbaldehyde

Guidance literature:: With pyridine; Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1039/b000751j

Reference yield:

: 70542-83-5
ethyl (2E)-5-(benzyloxy)pent-2-enoate

: 203520-18-7
2''-[(E)-(4R,5S,6R,8R,9S,13R,14R,15R)-14-(tert-Butyl-dimethyl-silanyloxy)-17-(tert-butyl-diphenyl-silanyloxy)-4,8-dimethoxy-6-methoxymethoxy-5,9,13,15-tetramethyl-12-oxo-heptadec-1-enyl]-[2,4';2',4'']teroxazole-4-carbaldehyde

Guidance literature:: Multi-step reaction with 28 steps

1.1: 84 percent / DIBAL-H / tetrahydrofuran; hexane / 2 h / 0 °C

2.1: Ti(O-i-Pr)4; (-)-diethyl tartrate; 4 Angstroem molecular sieves / CH₂Cl₂ / 0.5 h / -20 °C

2.2: 61 percent / t-BuOOH / CH₂Cl₂; 2,2,4-trimethyl-pentane / -20 °C

3.1: CuI / tetrahydrofuran / 0.5 h / -20 °C

3.2: 66 percent / tetrahydrofuran / 2.5 h / -20 °C

4.1: 94 percent / imidazole / dimethylformamide / 20 °C

5.1: NaH / dimethylformamide / 0.08 h / 0 °C

5.2: 66 percent / dimethylformamide / 2 h / 20 °C

6.1: 92 percent / H₂ / Pearlman's catalyst / methanol / 18 h

7.1: 87 percent / DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / 1.5 h / -78 °C

8.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / 1.5 h / -78 - 0 °C

8.2: 70 percent / CH₂Cl₂ / 3.5 h / -78 - 0 °C

9.1: 90 percent / LiBH₄ / tetrahydrofuran; methanol / 0.5 h / 0 °C

10.1: 90 percent / (i-Pr)2NEt / CH₂Cl₂ / 2 h / 0 - 20 °C

11.1: 82 percent / LiBH₄ / methanol; tetrahydrofuran / 1.5 h / 0 °C

12.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 - 20 °C

13.1: 80 percent / O₃ / CH₂Cl₂ / -78 °C

14.1: (+)-IPC₂BOMe / diethyl ether / 2 h / -78 - 20 °C

14.2: 70 percent / diethyl ether / 5 h / -78 °C

15.1: 95 percent / 2,6-di-tert-butylpyridine / CHCl₃ / 1.17 h / Heating

16.1: 90 percent / pyridinium toluene-p-sulfonate / ethanol / 9 h / Heating

17.1: 95 percent / (i-Pr)2NEt / CH₂Cl₂ / 3 h / Heating

18.1: O₃ / CH₂Cl₂ / 0.17 h / -78 °C

18.2: 89 percent / PPh₃ / CH₂Cl₂ / 0.25 h / -78 °C

19.1: 98 percent / p-TsOH / methanol / 1 h / 20 °C

20.1: 98 percent / TBAF / tetrahydrofuran / 6 h / 20 °C

21.1: 89 percent / N-methylmorpholine N-oxide; 4 Angstroem molecular sieves / TPAP / CH₂Cl₂ / 1 h / 20 °C

22.1: Ba(OH)2*8H₂O / tetrahydrofuran / 0.5 h / 20 °C

22.2: 95 percent / tetrahydrofuran; H₂O / 3.5 h / 20 °C

23.1: 94 percent / H₂ / Pearlman's catalyst / methanol

24.1: 94 percent / imidazole / dimethylformamide / 14 h / 20 °C

25.1: 95 percent / dimethylboryl bromide / CH₂Cl₂; diethyl ether / 1 h / -78 °C

26.1: n-BuLi / hexane; tetrahydrofuran / 1.5 h / 20 °C

26.2: 70 percent / tetrahydrofuran; hexane / 2 h / 20 °C

27.1: 75 percent / DIBAL-H / toluene; tetrahydrofuran / 2.75 h / 0 - 20 °C

28.1: 98 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 1 h / 20 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; barium dihydroxide; copper(l) iodide; lithium borohydride; n-butyllithium; 2,6-di-tert-butyl-pyridine; oxalyl dichloride; dimethylboron bromide; 4 A molecular sieve; di-n-butylboryl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; ozone; dimethyl sulfoxide; 4-methylmorpholine N-oxide; (-)-diethyl tartrate; triethylamine; N-ethyl-N,N-diisopropylamine; (+)-B-methoxydiisocamphenylborane; palladium dihydroxide; tetrapropylammonium perruthennate; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene; 1.1: Reduction / 2.1: Substitution / 2.2: Epoxidation / 3.1: Transmetallation / 3.2: Methylation / 4.1: Substitution / 5.1: Metallation / 5.2: Methylation / 6.1: Hydrogenolysis / 7.1: Oxidation / 8.1: Addition / 8.2: Condensation / 9.1: Reduction / 10.1: Substitution / 11.1: Reduction / 12.1: Substitution / 13.1: Oxidation / 14.1: Addition / 14.2: Addition / 15.1: Etherification / 16.1: Substitution / 17.1: Etherification / 18.1: Oxidation / 18.2: Elimination / 19.1: Addition / 20.1: Substitutio;
DOI:10.1039/b000751j

Reference yield:

: 89956-14-9
[3-(2-Benzyloxyethyl)oxiran-2-yl]methanol

: 203520-18-7
2''-[(E)-(4R,5S,6R,8R,9S,13R,14R,15R)-14-(tert-Butyl-dimethyl-silanyloxy)-17-(tert-butyl-diphenyl-silanyloxy)-4,8-dimethoxy-6-methoxymethoxy-5,9,13,15-tetramethyl-12-oxo-heptadec-1-enyl]-[2,4';2',4'']teroxazole-4-carbaldehyde

Guidance literature:: Multi-step reaction with 26 steps

1.1: CuI / tetrahydrofuran / 0.5 h / -20 °C

1.2: 66 percent / tetrahydrofuran / 2.5 h / -20 °C

2.1: 94 percent / imidazole / dimethylformamide / 20 °C

3.1: NaH / dimethylformamide / 0.08 h / 0 °C

3.2: 66 percent / dimethylformamide / 2 h / 20 °C

4.1: 92 percent / H₂ / Pearlman's catalyst / methanol / 18 h

5.1: 87 percent / DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / 1.5 h / -78 °C

6.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / 1.5 h / -78 - 0 °C

6.2: 70 percent / CH₂Cl₂ / 3.5 h / -78 - 0 °C

7.1: 90 percent / LiBH₄ / tetrahydrofuran; methanol / 0.5 h / 0 °C

8.1: 90 percent / (i-Pr)2NEt / CH₂Cl₂ / 2 h / 0 - 20 °C

9.1: 82 percent / LiBH₄ / methanol; tetrahydrofuran / 1.5 h / 0 °C

10.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 - 20 °C

11.1: 80 percent / O₃ / CH₂Cl₂ / -78 °C

12.1: (+)-IPC₂BOMe / diethyl ether / 2 h / -78 - 20 °C

12.2: 70 percent / diethyl ether / 5 h / -78 °C

13.1: 95 percent / 2,6-di-tert-butylpyridine / CHCl₃ / 1.17 h / Heating

14.1: 90 percent / pyridinium toluene-p-sulfonate / ethanol / 9 h / Heating

15.1: 95 percent / (i-Pr)2NEt / CH₂Cl₂ / 3 h / Heating

16.1: O₃ / CH₂Cl₂ / 0.17 h / -78 °C

16.2: 89 percent / PPh₃ / CH₂Cl₂ / 0.25 h / -78 °C

17.1: 98 percent / p-TsOH / methanol / 1 h / 20 °C

18.1: 98 percent / TBAF / tetrahydrofuran / 6 h / 20 °C

19.1: 89 percent / N-methylmorpholine N-oxide; 4 Angstroem molecular sieves / TPAP / CH₂Cl₂ / 1 h / 20 °C

20.1: Ba(OH)2*8H₂O / tetrahydrofuran / 0.5 h / 20 °C

20.2: 95 percent / tetrahydrofuran; H₂O / 3.5 h / 20 °C

21.1: 94 percent / H₂ / Pearlman's catalyst / methanol

22.1: 94 percent / imidazole / dimethylformamide / 14 h / 20 °C

23.1: 95 percent / dimethylboryl bromide / CH₂Cl₂; diethyl ether / 1 h / -78 °C

24.1: n-BuLi / hexane; tetrahydrofuran / 1.5 h / 20 °C

24.2: 70 percent / tetrahydrofuran; hexane / 2 h / 20 °C

25.1: 75 percent / DIBAL-H / toluene; tetrahydrofuran / 2.75 h / 0 - 20 °C

26.1: 98 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 1 h / 20 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; barium dihydroxide; copper(l) iodide; lithium borohydride; n-butyllithium; 2,6-di-tert-butyl-pyridine; oxalyl dichloride; dimethylboron bromide; 4 A molecular sieve; di-n-butylboryl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; ozone; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; (+)-B-methoxydiisocamphenylborane; palladium dihydroxide; tetrapropylammonium perruthennate; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene; 1.1: Transmetallation / 1.2: Methylation / 2.1: Substitution / 3.1: Metallation / 3.2: Methylation / 4.1: Hydrogenolysis / 5.1: Oxidation / 6.1: Addition / 6.2: Condensation / 7.1: Reduction / 8.1: Substitution / 9.1: Reduction / 10.1: Substitution / 11.1: Oxidation / 12.1: Addition / 12.2: Addition / 13.1: Etherification / 14.1: Substitution / 15.1: Etherification / 16.1: Oxidation / 16.2: Elimination / 17.1: Addition / 18.1: Substitution / 19.1: Oxidation / 20.1: Hydrolysis / 20.2: Condensatio;
DOI:10.1039/b000751j