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-carboxylic acid methyl ester

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-carboxylic acid methyl ester
CAS No.:203520-15-4
Molecular Formula:C₅₈H₈₅N₃O₁₂Si₂
Molecular Weight:1072.5
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-carboxylic acid methyl ester

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-carboxylic acid methyl ester

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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-carboxylic acid methyl ester

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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-carboxylic acid methyl ester

There total 37 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-carboxylic 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: 70.0%

: 203520-14-3
13-(tert-Butyldimethylsilanyloxy)-16-(tert-butyldiphenylsilanyloxy)-3,7-dimethoxy-5-methoxymethoxy-4,8,12,14-tetramethyl-11-oxohexadecanal

: 4''-Methoxycarbonyl-4,2':4',2''-ter(1,3-oxazolyl)-2-ylmethyltriphenylphosphonium bromide

: 203520-15-4
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-carboxylic acid methyl ester

Guidance literature:: With n-butyllithium; In tetrahydrofuran; -78 deg C to rt;
DOI:10.1055/s-1997-1055

Reference yield:

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

: 203520-15-4
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-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 26 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

With 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; 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; 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

: 203520-15-4
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-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 24 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

With 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; 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; 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