1-(tert-butyldiphenylsilyloxy)-5-(1,6-dioxaspiro[4.5]dec-9-en-2-yl)-pentan-3-ol

Base Information

Chemical Name:1-(tert-butyldiphenylsilyloxy)-5-(1,6-dioxaspiro[4.5]dec-9-en-2-yl)-pentan-3-ol
CAS No.:347189-49-5
Molecular Formula:C₂₉H₄₀O₄Si
Molecular Weight:480.72
Hs Code.:

Synonyms:1-(tert-butyldiphenylsilyloxy)-5-(1,6-dioxaspiro[4.5]dec-9-en-2-yl)-pentan-3-ol

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Chemical Property of 1-(tert-butyldiphenylsilyloxy)-5-(1,6-dioxaspiro[4.5]dec-9-en-2-yl)-pentan-3-ol

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Technology Process of 1-(tert-butyldiphenylsilyloxy)-5-(1,6-dioxaspiro[4.5]dec-9-en-2-yl)-pentan-3-ol

There total 13 articles about 1-(tert-butyldiphenylsilyloxy)-5-(1,6-dioxaspiro[4.5]dec-9-en-2-yl)-pentan-3-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: 79.0%

: 347189-48-4
4-{5-[5-(tert-butyldiphenylsilyloxy)-3-hydroxypentyl]-2-methoxytetrahydrofuran-2-yl}but-3-yn-1-ol

: 347189-49-5
1-(tert-butyldiphenylsilyloxy)-5-(1,6-dioxaspiro[4.5]dec-9-en-2-yl)-pentan-3-ol

Guidance literature:: 4-{5-[5-(tert-butyldiphenylsilyloxy)-3-hydroxypentyl]-2-methoxytetrahydrofuran-2-yl}but-3-yn-1-ol; With hydrogen; Lindlar's catalyst; In tetrahydrofuran; at 25 ℃; for 3h;

With pyridinium p-toluenesulfonate; In tetrahydrofuran; dichloromethane; for 0.0833333h;
DOI:10.1016/S0040-4020(01)00272-1

Reference yield:

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

: 347189-49-5
1-(tert-butyldiphenylsilyloxy)-5-(1,6-dioxaspiro[4.5]dec-9-en-2-yl)-pentan-3-ol

Guidance literature:: Multi-step reaction with 12 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

10.1: 80 percent / tetra-n-propylammonium perruthenate; N-methylmorpholine-N-oxide; molecular sieves 4A / CH₂Cl₂ / 0.5 h / 25 °C

11.1: 55 percent / camphorsulphonic acid / 1 h / 25 °C

12.1: hydrogen / Lindlar catalyst / tetrahydrofuran / 3 h / 25 °C

12.2: 79 percent / pyridinium p-toluenesulphonate / tetrahydrofuran; CH₂Cl₂ / 0.08 h

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; n-butyllithium; tetrapropylammonium perruthennate; oxalyl dichloride; dimethylsulfide borane complex; 4 A molecular sieve; camphor-10-sulfonic acid; hydrogen; Dess-Martin periodane; magnesium; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; Lindlar's catalyst; 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

: 347189-49-5
1-(tert-butyldiphenylsilyloxy)-5-(1,6-dioxaspiro[4.5]dec-9-en-2-yl)-pentan-3-ol

Guidance literature:: Multi-step reaction with 13 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

11.1: 80 percent / tetra-n-propylammonium perruthenate; N-methylmorpholine-N-oxide; molecular sieves 4A / CH₂Cl₂ / 0.5 h / 25 °C

12.1: 55 percent / camphorsulphonic acid / 1 h / 25 °C

13.1: hydrogen / Lindlar catalyst / tetrahydrofuran / 3 h / 25 °C

13.2: 79 percent / pyridinium p-toluenesulphonate / tetrahydrofuran; CH₂Cl₂ / 0.08 h

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; n-butyllithium; tetrapropylammonium perruthennate; oxalyl dichloride; dimethylsulfide borane complex; 4 A molecular sieve; camphor-10-sulfonic acid; hydrogen; Dess-Martin periodane; magnesium; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; Lindlar's catalyst; 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