4-(tert-butyl-dimethyl-silanyloxy)-2-ethylsulfanyl-3,5-dimethyl-6-[2,6,12-tris-(tert-butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyloxy)-5,7,9,11,13,15-hexamethyl-nonadeca-3,8,16,18-tetraenyl]-tetrahydro-pyran

Base Information

Chemical Name:4-(tert-butyl-dimethyl-silanyloxy)-2-ethylsulfanyl-3,5-dimethyl-6-[2,6,12-tris-(tert-butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyloxy)-5,7,9,11,13,15-hexamethyl-nonadeca-3,8,16,18-tetraenyl]-tetrahydro-pyran
CAS No.:303728-16-7
Molecular Formula:C₆₆H₁₂₄O₇SSi₄
Molecular Weight:1174.11
Hs Code.:

4-(<i>tert</i>-butyl-dimethyl-silanyloxy)-2-ethylsulfanyl-3,5-dimethyl-6-[2,6,12-tris-(<i>tert</i>-butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyloxy)-5,7,9,11,13,15-hexamethyl-nonadeca-3,8,16,18-tetraenyl]-tetrahydro-pyran

Synonyms:4-(tert-butyl-dimethyl-silanyloxy)-2-ethylsulfanyl-3,5-dimethyl-6-[2,6,12-tris-(tert-butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyloxy)-5,7,9,11,13,15-hexamethyl-nonadeca-3,8,16,18-tetraenyl]-tetrahydro-pyran

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Chemical Property of 4-(tert-butyl-dimethyl-silanyloxy)-2-ethylsulfanyl-3,5-dimethyl-6-[2,6,12-tris-(tert-butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyloxy)-5,7,9,11,13,15-hexamethyl-nonadeca-3,8,16,18-tetraenyl]-tetrahydro-pyran

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Technology Process of 4-(tert-butyl-dimethyl-silanyloxy)-2-ethylsulfanyl-3,5-dimethyl-6-[2,6,12-tris-(tert-butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyloxy)-5,7,9,11,13,15-hexamethyl-nonadeca-3,8,16,18-tetraenyl]-tetrahydro-pyran

There total 17 articles about 4-(tert-butyl-dimethyl-silanyloxy)-2-ethylsulfanyl-3,5-dimethyl-6-[2,6,12-tris-(tert-butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyloxy)-5,7,9,11,13,15-hexamethyl-nonadeca-3,8,16,18-tetraenyl]-tetrahydro-pyran 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:

: 2741-38-0
allyldiphenylphosphine

: 303728-15-6
5,11,15-tris-(tert-butyl-dimethyl-silanyloxy)-16-[4-(tert-butyl-dimethyl-silanyloxy)-6-ethylsulfanyl-3,5-dimethyl-tetrahydro-pyran-2-yl]-3-(4-methoxy-benzyloxy)-2,4,6,8,10,12-hexamethyl-hexadeca-8,13-dienal

: 303728-16-7
4-(tert-butyl-dimethyl-silanyloxy)-2-ethylsulfanyl-3,5-dimethyl-6-[2,6,12-tris-(tert-butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyloxy)-5,7,9,11,13,15-hexamethyl-nonadeca-3,8,16,18-tetraenyl]-tetrahydro-pyran

: 4-(tert-butyl-dimethyl-silanyloxy)-2-ethylsulfanyl-3,5-dimethyl-6-[2,6,12-tris-(tert-butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyloxy)-5,7,9,11,13,15-hexamethyl-nonadeca-3,8,16,18-tetraenyl]-tetrahydro-pyran

Guidance literature:: allyldiphenylphosphine; With titanium(IV) isopropylate; tert.-butyl lithium; In tetrahydrofuran; pentane; at -78 - 0 ℃;

5,11,15-tris-(tert-butyl-dimethyl-silanyloxy)-16-[4-(tert-butyl-dimethyl-silanyloxy)-6-ethylsulfanyl-3,5-dimethyl-tetrahydro-pyran-2-yl]-3-(4-methoxy-benzyloxy)-2,4,6,8,10,12-hexamethyl-hexadeca-8,13-dienal; With methyl iodide; In tetrahydrofuran; pentane; at 20 ℃; Further stages.;
DOI:10.1021/ja0015287

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 303728-16-7
4-(tert-butyl-dimethyl-silanyloxy)-2-ethylsulfanyl-3,5-dimethyl-6-[2,6,12-tris-(tert-butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyloxy)-5,7,9,11,13,15-hexamethyl-nonadeca-3,8,16,18-tetraenyl]-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 11 steps

1.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h

2.1: 100 percent / DIBAL / tetrahydrofuran; hexane / 3.5 h / -78 °C

3.1: n-BuLi / tetrahydrofuran

4.1: t-BuLi / diethyl ether / 0.17 h / -78 °C

4.2: MgBr₂ / diethyl ether

4.3: 14 percent / PdCl₂(dppf) / diethyl ether / 20 °C

5.1: 98 percent / DDQ; H₂O / CH₂Cl₂ / 3 h

6.1: I₂; PPh₃; imidazole / benzene; diethyl ether / 2 h

7.1: i-Pr₂NEt / 24 h / 80 °C

8.1: NaHMDS / tetrahydrofuran / -78 - 0 °C

8.2: 76 percent / tetrahydrofuran / 2 h / -78 - 20 °C

9.1: 88 percent / DIBAL / CH₂Cl₂; toluene / -78 - 0 °C

10.1: 96 percent / DMSO; SO₃*pyridine; Et₃N / CH₂Cl₂ / 0.75 h / 0 °C

11.1: t-BuLi; Ti(O-i-Pr)4 / tetrahydrofuran; pentane / -78 - 0 °C

11.2: MeI / tetrahydrofuran; pentane / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; n-butyllithium; pyridine-SO₃ complex; water; iodine; tert.-butyl lithium; sodium hexamethyldisilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; pentane; benzene; 1.1: silylation / 2.1: Reduction / 3.1: Condensation / 4.1: Metallation / 4.2: transmetallation / 4.3: Substitution / 5.1: ether cleavage / 6.1: Iodination / 7.1: Cyclization / 8.1: Metallation / 8.2: Condensation / 9.1: Ring cleavage / 10.1: Oxidation / 11.1: Metallation / 11.2: Condensation;
DOI:10.1021/ja0015287

Reference yield:

: 132969-62-1
(2'R,3'S,4'S,4R,5S)-3-[3'-hydroxy-5'-(4-methoxyphenyl)methoxy-2',4'-dimethylpentanoyl]-5-phenyl-4-methyl-2-oxazolidinone

: 303728-16-7
4-(tert-butyl-dimethyl-silanyloxy)-2-ethylsulfanyl-3,5-dimethyl-6-[2,6,12-tris-(tert-butyl-dimethyl-silanyloxy)-14-(4-methoxy-benzyloxy)-5,7,9,11,13,15-hexamethyl-nonadeca-3,8,16,18-tetraenyl]-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 12 steps

1.1: AlMe₃ / tetrahydrofuran; hexane / 0 - 20 °C

1.2: 98 percent / tetrahydrofuran; hexane / 2.5 h / -20 °C

2.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h

3.1: 100 percent / DIBAL / tetrahydrofuran; hexane / 3.5 h / -78 °C

4.1: n-BuLi / tetrahydrofuran

5.1: t-BuLi / diethyl ether / 0.17 h / -78 °C

5.2: MgBr₂ / diethyl ether

5.3: 14 percent / PdCl₂(dppf) / diethyl ether / 20 °C

6.1: 98 percent / DDQ; H₂O / CH₂Cl₂ / 3 h

7.1: I₂; PPh₃; imidazole / benzene; diethyl ether / 2 h

8.1: i-Pr₂NEt / 24 h / 80 °C

9.1: NaHMDS / tetrahydrofuran / -78 - 0 °C

9.2: 76 percent / tetrahydrofuran / 2 h / -78 - 20 °C

10.1: 88 percent / DIBAL / CH₂Cl₂; toluene / -78 - 0 °C

11.1: 96 percent / DMSO; SO₃*pyridine; Et₃N / CH₂Cl₂ / 0.75 h / 0 °C

12.1: t-BuLi; Ti(O-i-Pr)4 / tetrahydrofuran; pentane / -78 - 0 °C

12.2: MeI / tetrahydrofuran; pentane / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; n-butyllithium; pyridine-SO₃ complex; water; iodine; trimethylaluminum; tert.-butyl lithium; sodium hexamethyldisilazane; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; pentane; benzene; 1.1: Metallation / 1.2: Substitution / 2.1: silylation / 3.1: Reduction / 4.1: Condensation / 5.1: Metallation / 5.2: transmetallation / 5.3: Substitution / 6.1: ether cleavage / 7.1: Iodination / 8.1: Cyclization / 9.1: Metallation / 9.2: Condensation / 10.1: Ring cleavage / 11.1: Oxidation / 12.1: Metallation / 12.2: Condensation;
DOI:10.1021/ja0015287