(3S,4R,5S)-6-benzyloxy-4-(tert-butyldimethylsilanyloxy)-3,5-dimethyltrimethylsilanylhex-1-yne

Base Information

Chemical Name:(3S,4R,5S)-6-benzyloxy-4-(tert-butyldimethylsilanyloxy)-3,5-dimethyltrimethylsilanylhex-1-yne
CAS No.:444109-28-8
Molecular Formula:C₂₄H₄₂O₂Si₂
Molecular Weight:418.767
Hs Code.:

Synonyms:(3S,4R,5S)-6-benzyloxy-4-(tert-butyldimethylsilanyloxy)-3,5-dimethyltrimethylsilanylhex-1-yne

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Chemical Property of (3S,4R,5S)-6-benzyloxy-4-(tert-butyldimethylsilanyloxy)-3,5-dimethyltrimethylsilanylhex-1-yne

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Technology Process of (3S,4R,5S)-6-benzyloxy-4-(tert-butyldimethylsilanyloxy)-3,5-dimethyltrimethylsilanylhex-1-yne

There total 7 articles about (3S,4R,5S)-6-benzyloxy-4-(tert-butyldimethylsilanyloxy)-3,5-dimethyltrimethylsilanylhex-1-yne 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%

: 75-77-4
chloro-trimethyl-silane

: 444109-27-7
(2S,3R,4S)-1-benzyloxy-3-(tert-butyldimethylsilanyloxy)-6,6-dibromo-2,4-dimethyl-hex-5-ene

: 444109-28-8
(3S,4R,5S)-6-benzyloxy-4-(tert-butyldimethylsilanyloxy)-3,5-dimethyltrimethylsilanylhex-1-yne

Guidance literature:: (2S,3R,4S)-1-benzyloxy-3-(tert-butyldimethylsilanyloxy)-6,6-dibromo-2,4-dimethyl-hex-5-ene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - -20 ℃;

chloro-trimethyl-silane; In tetrahydrofuran; hexane; at -78 - 0 ℃; for 8h;
DOI:10.1021/ja043168j

Reference yield:

: 79027-28-4
(2S)-3-(benzyloxy)-2-methylpropanal

: 444109-28-8
(3S,4R,5S)-6-benzyloxy-4-(tert-butyldimethylsilanyloxy)-3,5-dimethyltrimethylsilanylhex-1-yne

Guidance literature:: Multi-step reaction with 5 steps

1.1: 85 percent / TiCl₄ / CH₂Cl₂ / -78 - -20 °C

2.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / -78 - 20 °C

3.1: ozone / methanol / -78 °C

3.2: dimethyl sulfide / methanol / -78 - 0 °C

4.1: 10.7 g / triphenylphosphine; 2,6-lutidine / CH₂Cl₂ / 4 h / 0 °C

5.1: n-butyllithium / tetrahydrofuran; hexane / -78 - -20 °C

5.2: 79 percent / tetrahydrofuran; hexane / 8 h / -78 - 0 °C

With 2,6-dimethylpyridine; n-butyllithium; titanium tetrachloride; ozone; triphenylphosphine; In tetrahydrofuran; methanol; hexane; dichloromethane; 4.1: Corey-Fuchs olefination;
DOI:10.1021/ja043168j

Reference yield:

: 444109-42-6
(2S,3R,4S)-5-benzyloxy-3-(tert-butyldimethylsilyloxy)-2,4-dimethyl-pentanal

: 444109-28-8
(3S,4R,5S)-6-benzyloxy-4-(tert-butyldimethylsilanyloxy)-3,5-dimethyltrimethylsilanylhex-1-yne

Guidance literature:: Multi-step reaction with 2 steps

1.1: 10.7 g / triphenylphosphine; 2,6-lutidine / CH₂Cl₂ / 4 h / 0 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / -78 - -20 °C

2.2: 79 percent / tetrahydrofuran; hexane / 8 h / -78 - 0 °C

With 2,6-dimethylpyridine; n-butyllithium; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; 1.1: Corey-Fuchs olefination;
DOI:10.1021/ja043168j