(4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-4-((tert-butyldimethylsilyloxy)methyl)-2-phenyl-6-vinyl-5,6-dihydro-4H-1,3-oxazine

Base Information

Chemical Name:(4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-4-((tert-butyldimethylsilyloxy)methyl)-2-phenyl-6-vinyl-5,6-dihydro-4H-1,3-oxazine
CAS No.:1349697-11-5
Molecular Formula:C₂₅H₄₃NO₃Si₂
Molecular Weight:461.792
Hs Code.:

Synonyms:(4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-4-((tert-butyldimethylsilyloxy)methyl)-2-phenyl-6-vinyl-5,6-dihydro-4H-1,3-oxazine

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Chemical Property of (4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-4-((tert-butyldimethylsilyloxy)methyl)-2-phenyl-6-vinyl-5,6-dihydro-4H-1,3-oxazine

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Technology Process of (4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-4-((tert-butyldimethylsilyloxy)methyl)-2-phenyl-6-vinyl-5,6-dihydro-4H-1,3-oxazine

There total 9 articles about (4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-4-((tert-butyldimethylsilyloxy)methyl)-2-phenyl-6-vinyl-5,6-dihydro-4H-1,3-oxazine 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: 85.0%

: C₂₅H₄₄ClNO₃Si₂

: 1349697-11-5
(4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-4-((tert-butyldimethylsilyloxy)methyl)-2-phenyl-6-vinyl-5,6-dihydro-4H-1,3-oxazine

Guidance literature:: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; at 50 ℃; Inert atmosphere;
DOI:10.1016/j.tet.2019.06.005

Reference yield:

: 1349697-05-7
N-((5S,6R)-5-((E)-3-chloroprop-1-enyl)-2,2,3,3,9,9,10,10-octamethyl-4,8-dioxa-3,9-disilaundecan-6-yl)benzamide

: 1349697-11-5
(4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-4-((tert-butyldimethylsilyloxy)methyl)-2-phenyl-6-vinyl-5,6-dihydro-4H-1,3-oxazine

Guidance literature:: N-((5S,6R)-5-((E)-3-chloroprop-1-enyl)-2,2,3,3,9,9,10,10-octamethyl-4,8-dioxa-3,9-disilaundecan-6-yl)benzamide; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; for 0.0833333h;

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; mineral oil; at 0 ℃; for 5h; optical yield given as %de; diastereoselective reaction;
DOI:10.1016/j.tet.2011.09.084

Reference yield:

(R)-methyl 2-benzamido-3-(tert-butyldimethylsilyloxy)propanoate: 1029529-45-0
(R)-methyl 2-benzamido-3-(tert-butyldimethylsilyloxy)propanoate

: 1349697-11-5
(4R,5R,6R)-5-(tert-butyldimethylsilyloxy)-4-((tert-butyldimethylsilyloxy)methyl)-2-phenyl-6-vinyl-5,6-dihydro-4H-1,3-oxazine

Guidance literature:: Multi-step reaction with 5 steps

1.1: trimethylaluminum / hexane; dichloromethane / 0.5 h / 20 °C

1.2: 1 h / 20 °C

2.1: methyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: 0.5 h / -78 °C

3.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran; ethanol / 2 h / -78 °C

3.2: -78 °C

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

5.1: sodium hydride / tetrahydrofuran; mineral oil / 0.08 h / 0 °C

5.2: 5 h / 0 °C

With 1H-imidazole; methyllithium; trimethylaluminum; sodium hydride; lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; mineral oil;
DOI:10.1016/j.tet.2011.09.084