1,11-bis-(tert-butyldimethylsilyloxy)-13-(tert-butyldiphenylsilyloxy)-8-triethylsilyloxytridec-3-yn-5-ol

Base Information

Chemical Name:1,11-bis-(tert-butyldimethylsilyloxy)-13-(tert-butyldiphenylsilyloxy)-8-triethylsilyloxytridec-3-yn-5-ol
CAS No.:347189-38-2
Molecular Formula:C₄₇H₈₄O₅Si₄
Molecular Weight:841.523
Hs Code.:

Synonyms:1,11-bis-(tert-butyldimethylsilyloxy)-13-(tert-butyldiphenylsilyloxy)-8-triethylsilyloxytridec-3-yn-5-ol

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Chemical Property of 1,11-bis-(tert-butyldimethylsilyloxy)-13-(tert-butyldiphenylsilyloxy)-8-triethylsilyloxytridec-3-yn-5-ol

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Technology Process of 1,11-bis-(tert-butyldimethylsilyloxy)-13-(tert-butyldiphenylsilyloxy)-8-triethylsilyloxytridec-3-yn-5-ol

There total 11 articles about 1,11-bis-(tert-butyldimethylsilyloxy)-13-(tert-butyldiphenylsilyloxy)-8-triethylsilyloxytridec-3-yn-5-ol 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: 86.0%

: 78592-82-2
4-(tert-butyldimethylsilyloxy)-1-butyne

: 347189-37-1
7-(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)-4-triethylsilyloxynonal

: 347189-38-2
1,11-bis-(tert-butyldimethylsilyloxy)-13-(tert-butyldiphenylsilyloxy)-8-triethylsilyloxytridec-3-yn-5-ol

Guidance literature:: 4-(tert-butyldimethylsilyloxy)-1-butyne; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 1h;

7-(tert-butyldimethylsilyloxy)-9-(tert-butyldiphenylsilyloxy)-4-triethylsilyloxynonal; In tetrahydrofuran; hexane; at -78 - 25 ℃;
DOI:10.1016/S0040-4020(01)00272-1

Reference yield:

: 112897-03-7
3-(tert-butyldiphenylsilyloxy)-1-propanal

: 347189-38-2
1,11-bis-(tert-butyldimethylsilyloxy)-13-(tert-butyldiphenylsilyloxy)-8-triethylsilyloxytridec-3-yn-5-ol

Guidance literature:: Multi-step reaction with 9 steps

1.1: magnesium / diethyl ether / 0.5 h / 20 °C

1.2: 94 percent / diethyl ether / 0 - 20 °C

2.1: 81 percent / 4-(dimethylamino)pyridine; imidazole / CH₂Cl₂ / 12 h / 20 °C

3.1: borane-dimethyl sulfide / tetrahydrofuran / 0 - 25 °C

3.2: 82 percent / sodium hydroxide; hydrogen peroxide / tetrahydrofuran

4.1: 95 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -78 - 25 °C

5.1: magnesium / diethyl ether / 0.5 h / 20 °C

5.2: 90 percent / diethyl ether / 0 - 20 °C

6.1: 86 percent / 2,6-lutidine / CH₂Cl₂ / 12 h / 25 °C

7.1: borane-dimethyl sulfide / tetrahydrofuran / 0 - 25 °C

7.2: 82 percent / sodium hydroxide; hydrogen peroxide / tetrahydrofuran

8.1: 73 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 2 h

9.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C

9.2: 86 percent / tetrahydrofuran; hexane / -78 - 25 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; n-butyllithium; oxalyl dichloride; dimethylsulfide borane complex; Dess-Martin periodane; magnesium; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 1.2: Grignard addition / 4.1: Swern oxidation / 5.2: Grignard addition;
DOI:10.1016/S0040-4020(01)00272-1

Reference yield:

: 127047-71-6
3-(tert-butyldiphenylsilyloxy)propan-1-ol

: 347189-38-2
1,11-bis-(tert-butyldimethylsilyloxy)-13-(tert-butyldiphenylsilyloxy)-8-triethylsilyloxytridec-3-yn-5-ol

Guidance literature:: Multi-step reaction with 10 steps

1.1: 90 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -78 - 25 °C

2.1: magnesium / diethyl ether / 0.5 h / 20 °C

2.2: 94 percent / diethyl ether / 0 - 20 °C

3.1: 81 percent / 4-(dimethylamino)pyridine; imidazole / CH₂Cl₂ / 12 h / 20 °C

4.1: borane-dimethyl sulfide / tetrahydrofuran / 0 - 25 °C

4.2: 82 percent / sodium hydroxide; hydrogen peroxide / tetrahydrofuran

5.1: 95 percent / oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / -78 - 25 °C

6.1: magnesium / diethyl ether / 0.5 h / 20 °C

6.2: 90 percent / diethyl ether / 0 - 20 °C

7.1: 86 percent / 2,6-lutidine / CH₂Cl₂ / 12 h / 25 °C

8.1: borane-dimethyl sulfide / tetrahydrofuran / 0 - 25 °C

8.2: 82 percent / sodium hydroxide; hydrogen peroxide / tetrahydrofuran

9.1: 73 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 2 h

10.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C

10.2: 86 percent / tetrahydrofuran; hexane / -78 - 25 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; n-butyllithium; oxalyl dichloride; dimethylsulfide borane complex; Dess-Martin periodane; magnesium; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; 1.1: Swern oxidation / 2.2: Grignard addition / 5.1: Swern oxidation / 6.2: Grignard addition;
DOI:10.1016/S0040-4020(01)00272-1