(5S,6S)-9-(benzyloxy)-6-(tert-butyldimethylsilyloxy)-5-methylnon-2-yn-1-ol

Base Information

Chemical Name:(5S,6S)-9-(benzyloxy)-6-(tert-butyldimethylsilyloxy)-5-methylnon-2-yn-1-ol
CAS No.:1438888-02-8
Molecular Formula:C₂₃H₃₈O₃Si
Molecular Weight:390.638
Hs Code.:

Synonyms:(5S,6S)-9-(benzyloxy)-6-(tert-butyldimethylsilyloxy)-5-methylnon-2-yn-1-ol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (5S,6S)-9-(benzyloxy)-6-(tert-butyldimethylsilyloxy)-5-methylnon-2-yn-1-ol

Chemical Property:

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Technology Process of (5S,6S)-9-(benzyloxy)-6-(tert-butyldimethylsilyloxy)-5-methylnon-2-yn-1-ol

There total 8 articles about (5S,6S)-9-(benzyloxy)-6-(tert-butyldimethylsilyloxy)-5-methylnon-2-yn-1-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: 90.0%

: 1438887-88-7
((4S,5S)-1-(benzyloxy)-5-methyl-9-(tetrahydro-2H-pyran-2-yloxy)non-7-yn-4-yloxy)(tert-butyl)dimethylsilane

: 1438888-02-8
(5S,6S)-9-(benzyloxy)-6-(tert-butyldimethylsilyloxy)-5-methylnon-2-yn-1-ol

Guidance literature:: With boron trifluoride diethyl etherate; ethane-1,2-dithiol; In dichloromethane; at -20 ℃; for 0.5h;
DOI:10.1016/j.tetlet.2013.01.134

Reference yield:

: 5470-84-8
4-benzyloxybutanal

: 1438888-02-8
(5S,6S)-9-(benzyloxy)-6-(tert-butyldimethylsilyloxy)-5-methylnon-2-yn-1-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: titanium tetrachloride / dichloromethane / -15 °C

1.2: 0.5 h / -15 °C

1.3: 1 h / -15 °C

2.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C

3.1: sodium tetrahydroborate; methanol / 1 h

4.1: triphenylphosphine; carbon tetrabromide / acetonitrile / 2.08 h / 0 - 20 °C

5.1: N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium / tetrahydrofuran; hexane / 0.08 h / -45 - 30 °C

5.2: 5 h / -40 - 0 °C

6.1: boron trifluoride diethyl etherate; ethane-1,2-dithiol / dichloromethane / 0.5 h / -20 °C

With methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; n-butyllithium; carbon tetrabromide; boron trifluoride diethyl etherate; titanium tetrachloride; ethane-1,2-dithiol; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; acetonitrile;
DOI:10.1016/j.tetlet.2013.01.134

Reference yield:

: 4541-14-4
4-benzyloxy-butan-1-ol

: 1438888-02-8
(5S,6S)-9-(benzyloxy)-6-(tert-butyldimethylsilyloxy)-5-methylnon-2-yn-1-ol

Guidance literature:: Multi-step reaction with 7 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C

1.2: 1.5 h / -78 - 20 °C

2.1: titanium tetrachloride / dichloromethane / -15 °C

2.2: 0.5 h / -15 °C

2.3: 1 h / -15 °C

3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C

4.1: sodium tetrahydroborate; methanol / 1 h

5.1: triphenylphosphine; carbon tetrabromide / acetonitrile / 2.08 h / 0 - 20 °C

6.1: N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium / tetrahydrofuran; hexane / 0.08 h / -45 - 30 °C

6.2: 5 h / -40 - 0 °C

7.1: boron trifluoride diethyl etherate; ethane-1,2-dithiol / dichloromethane / 0.5 h / -20 °C

With methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; carbon tetrabromide; boron trifluoride diethyl etherate; titanium tetrachloride; ethane-1,2-dithiol; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; acetonitrile;
DOI:10.1016/j.tetlet.2013.01.134