(5S,7R,9S)-5-benzyloxy-11-tert-butyldimethylsilyloxy-4,4-dimethyl-7,9-dihydroxy-7,9-O-isopropylideneundec-1-yn-3-one

Base Information

Chemical Name:(5S,7R,9S)-5-benzyloxy-11-tert-butyldimethylsilyloxy-4,4-dimethyl-7,9-dihydroxy-7,9-O-isopropylideneundec-1-yn-3-one
CAS No.:1352746-51-0
Molecular Formula:C₂₉H₄₆O₅Si
Molecular Weight:502.767
Hs Code.:

Synonyms:(5S,7R,9S)-5-benzyloxy-11-tert-butyldimethylsilyloxy-4,4-dimethyl-7,9-dihydroxy-7,9-O-isopropylideneundec-1-yn-3-one

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Chemical Property of (5S,7R,9S)-5-benzyloxy-11-tert-butyldimethylsilyloxy-4,4-dimethyl-7,9-dihydroxy-7,9-O-isopropylideneundec-1-yn-3-one

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Technology Process of (5S,7R,9S)-5-benzyloxy-11-tert-butyldimethylsilyloxy-4,4-dimethyl-7,9-dihydroxy-7,9-O-isopropylideneundec-1-yn-3-one

There total 12 articles about (5S,7R,9S)-5-benzyloxy-11-tert-butyldimethylsilyloxy-4,4-dimethyl-7,9-dihydroxy-7,9-O-isopropylideneundec-1-yn-3-one 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:

: 1352746-50-9
C₂₉H₄₈O₅Si

: 1352746-51-0
(5S,7R,9S)-5-benzyloxy-11-tert-butyldimethylsilyloxy-4,4-dimethyl-7,9-dihydroxy-7,9-O-isopropylideneundec-1-yn-3-one

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 0.333333h; Inert atmosphere;
DOI:10.1016/j.tet.2011.09.064

Reference yield:

: 470470-80-5
(5S,7S)-7-benzyloxy-9-tert-butyldimethylsilyloxy-1-tert-butyldiphenylsilyloxy-5-hydroxy-8,8-dimethylnonan-3-one

: 1352746-51-0
(5S,7R,9S)-5-benzyloxy-11-tert-butyldimethylsilyloxy-4,4-dimethyl-7,9-dihydroxy-7,9-O-isopropylideneundec-1-yn-3-one

Guidance literature:: Multi-step reaction with 7 steps

1: lithium tri-t-butoxyaluminum hydride; lithium iodide / tetrahydrofuran; diethyl ether / 18 h / -78 °C / Inert atmosphere

2: pyridinium p-toluenesulfonate / 18 h / 20 °C / Inert atmosphere

3: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere

4: 1H-imidazole / dichloromethane / 0 °C

5: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

6: tetrahydrofuran / -78 - 20 °C / Inert atmosphere

7: Dess-Martin periodane / dichloromethane / 0.33 h / 20 °C / Inert atmosphere

With 1H-imidazole; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; Dess-Martin periodane; lithium tri-t-butoxyaluminum hydride; lithium iodide; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1016/j.tet.2011.09.064

Reference yield:

: 1352746-46-3
(3S,5R,7S)-7-benzyloxy-9-tert-butyldimethylsilyloxy-1-tert-butyldiphenylsilyloxy-8,8-dimethylnonane-3,5-diol

: 1352746-51-0
(5S,7R,9S)-5-benzyloxy-11-tert-butyldimethylsilyloxy-4,4-dimethyl-7,9-dihydroxy-7,9-O-isopropylideneundec-1-yn-3-one

Guidance literature:: Multi-step reaction with 6 steps

1: pyridinium p-toluenesulfonate / 18 h / 20 °C / Inert atmosphere

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere

3: 1H-imidazole / dichloromethane / 0 °C

4: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

5: tetrahydrofuran / -78 - 20 °C / Inert atmosphere

6: Dess-Martin periodane / dichloromethane / 0.33 h / 20 °C / Inert atmosphere

With 1H-imidazole; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; Dess-Martin periodane; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tet.2011.09.064