(4S,5R,6S)-4-(hydroxymethyl)-2-phenyl-6-(tetradec-1-enyl)-5,6-dihydro-4H-1,3-oxazin-5-ol

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Chemical Name:(4S,5R,6S)-4-(hydroxymethyl)-2-phenyl-6-(tetradec-1-enyl)-5,6-dihydro-4H-1,3-oxazin-5-ol
CAS No.:1380210-89-8
Molecular Formula:C₂₅H₃₉NO₃
Molecular Weight:401.59
Hs Code.:

Synonyms:(4S,5R,6S)-4-(hydroxymethyl)-2-phenyl-6-(tetradec-1-enyl)-5,6-dihydro-4H-1,3-oxazin-5-ol

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Chemical Property of (4S,5R,6S)-4-(hydroxymethyl)-2-phenyl-6-(tetradec-1-enyl)-5,6-dihydro-4H-1,3-oxazin-5-ol

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Technology Process of (4S,5R,6S)-4-(hydroxymethyl)-2-phenyl-6-(tetradec-1-enyl)-5,6-dihydro-4H-1,3-oxazin-5-ol

There total 9 articles about (4S,5R,6S)-4-(hydroxymethyl)-2-phenyl-6-(tetradec-1-enyl)-5,6-dihydro-4H-1,3-oxazin-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: 90.0%

: 1380210-80-9
(4S,5R,6S)-5-(tert-butyldimethylsilyloxy)-4-[(tert-butyldimethylsilyloxy)methyl]-2-phenyl-6-(tetradec-1-enyl)-5,6-dihydro-4H-1,3-oxazine

: 1380210-89-8
(4S,5R,6S)-4-(hydroxymethyl)-2-phenyl-6-(tetradec-1-enyl)-5,6-dihydro-4H-1,3-oxazin-5-ol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃; for 1h; Inert atmosphere;
DOI:10.1002/ejoc.201200064

Reference yield:

: 933468-31-6
N-benzoyl-O-((tert-butyl)-dimethylsilyl)-(S)-serine methyl ester

: 1380210-89-8
(4S,5R,6S)-4-(hydroxymethyl)-2-phenyl-6-(tetradec-1-enyl)-5,6-dihydro-4H-1,3-oxazin-5-ol

Guidance literature:: Multi-step reaction with 7 steps

1.1: trimethylaluminum / hexane; dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere

1.2: 20 °C / Inert atmosphere

2.1: methyllithium / tetrahydrofuran; hexane / -78 °C / Inert atmosphere

2.2: -78 °C / Inert atmosphere

3.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran; ethanol / 4 h / -78 °C / Inert atmosphere

4.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

5.1: tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran; mineral oil / 0.08 h / 50 °C / Inert atmosphere

5.2: 12 h / 50 °C / Inert atmosphere

6.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 8 h / Inert atmosphere; Reflux

7.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; tetrabutyl ammonium fluoride; methyllithium; trimethylaluminum; tetra-(n-butyl)ammonium iodide; sodium hydride; lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; mineral oil;
DOI:10.1002/ejoc.201200064

Reference yield:

: 933468-32-7
C₁₈H₃₀N₂O₄Si

: 1380210-89-8
(4S,5R,6S)-4-(hydroxymethyl)-2-phenyl-6-(tetradec-1-enyl)-5,6-dihydro-4H-1,3-oxazin-5-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: methyllithium / tetrahydrofuran; hexane / -78 °C / Inert atmosphere

1.2: -78 °C / Inert atmosphere

2.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran; ethanol / 4 h / -78 °C / Inert atmosphere

3.1: 1H-imidazole / N,N-dimethyl-formamide / 2 h / 20 °C / Inert atmosphere

4.1: tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran; mineral oil / 0.08 h / 50 °C / Inert atmosphere

4.2: 12 h / 50 °C / Inert atmosphere

5.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 8 h / Inert atmosphere; Reflux

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; tetrabutyl ammonium fluoride; methyllithium; tetra-(n-butyl)ammonium iodide; sodium hydride; lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; mineral oil;
DOI:10.1002/ejoc.201200064