(-)-(4R,6S,8R,9S,9aS)-6-(acetoxymethyl)-8,9-dihydroxy-4-phenyl-9a-(trifluoromethyl)hexahydropyrido[2,1-c][1,4]oxazin-1(6H)-one

Base Information

Chemical Name:(-)-(4R,6S,8R,9S,9aS)-6-(acetoxymethyl)-8,9-dihydroxy-4-phenyl-9a-(trifluoromethyl)hexahydropyrido[2,1-c][1,4]oxazin-1(6H)-one
CAS No.:1379671-76-7
Molecular Formula:C₁₈H₂₀F₃NO₆
Molecular Weight:403.355
Hs Code.:

Synonyms:(-)-(4R,6S,8R,9S,9aS)-6-(acetoxymethyl)-8,9-dihydroxy-4-phenyl-9a-(trifluoromethyl)hexahydropyrido[2,1-c][1,4]oxazin-1(6H)-one

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Chemical Property of (-)-(4R,6S,8R,9S,9aS)-6-(acetoxymethyl)-8,9-dihydroxy-4-phenyl-9a-(trifluoromethyl)hexahydropyrido[2,1-c][1,4]oxazin-1(6H)-one

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Technology Process of (-)-(4R,6S,8R,9S,9aS)-6-(acetoxymethyl)-8,9-dihydroxy-4-phenyl-9a-(trifluoromethyl)hexahydropyrido[2,1-c][1,4]oxazin-1(6H)-one

There total 5 articles about (-)-(4R,6S,8R,9S,9aS)-6-(acetoxymethyl)-8,9-dihydroxy-4-phenyl-9a-(trifluoromethyl)hexahydropyrido[2,1-c][1,4]oxazin-1(6H)-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: 89.0%

: 1379671-69-8
(-)-(4R,6S,9aS)-6-(acetoxymethyl)-4-phenyl-9a-(trifluoromethyl)-3,4,6,7-tetrahydropyrido[2,1-c][1,4]oxazin-1(9aH)-one

: 1379671-76-7
(-)-(4R,6S,8R,9S,9aS)-6-(acetoxymethyl)-8,9-dihydroxy-4-phenyl-9a-(trifluoromethyl)hexahydropyrido[2,1-c][1,4]oxazin-1(6H)-one

Guidance literature:: With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In 2-methyl-propan-1-ol; water; acetone; at 20 ℃; for 48h; diastereoselective reaction; Inert atmosphere;
DOI:10.1002/chem.201102351

Reference yield:

: 1009605-87-1
(2R,5R)-3-(pent-4-enyl)-5-phenyl-2-(trifluoromethyl)-5,6-dihydro-2H-1,4-oxazin-2-ol

: 1379671-76-7
(-)-(4R,6S,8R,9S,9aS)-6-(acetoxymethyl)-8,9-dihydroxy-4-phenyl-9a-(trifluoromethyl)hexahydropyrido[2,1-c][1,4]oxazin-1(6H)-one

Guidance literature:: Multi-step reaction with 4 steps

1: iodine; sodium hydride / tetrahydrofuran / 0.5 h / 60 °C / Inert atmosphere; Microwave irradiation

2: dimethyl sulfoxide / 12 h / 25 °C / Inert atmosphere

3: 24 h / 20 °C / Inert atmosphere

4: osmium(VIII) oxide; 4-methylmorpholine N-oxide / 2-methyl-propan-1-ol; water; acetone / 48 h / 20 °C / Inert atmosphere

With osmium(VIII) oxide; iodine; sodium hydride; 4-methylmorpholine N-oxide; In tetrahydrofuran; 2-methyl-propan-1-ol; water; dimethyl sulfoxide; acetone;
DOI:10.1002/chem.201102351

Reference yield:

: 1009605-77-9
(R)-3-(pent-4-enyl)-5-phenyl-5,6-dihydro-2H-1,4-oxazin-2-one

: 1379671-76-7
(-)-(4R,6S,8R,9S,9aS)-6-(acetoxymethyl)-8,9-dihydroxy-4-phenyl-9a-(trifluoromethyl)hexahydropyrido[2,1-c][1,4]oxazin-1(6H)-one

Guidance literature:: Multi-step reaction with 5 steps

1: tris(dimethylamino)sulfonium trimethylsilyldifluoride / tetrahydrofuran / 0 °C / Inert atmosphere

2: iodine; sodium hydride / tetrahydrofuran / 0.5 h / 60 °C / Inert atmosphere; Microwave irradiation

3: 1,8-diazabicyclo[5.4.0]undec-7-ene / dimethyl sulfoxide / 1 h / 60 °C / Inert atmosphere; Microwave irradiation

4: 24 h / 20 °C / Inert atmosphere

5: osmium(VIII) oxide; 4-methylmorpholine N-oxide / 2-methyl-propan-1-ol; water; acetone / 48 h / 20 °C / Inert atmosphere

With osmium(VIII) oxide; tris(dimethylamino)sulfonium trimethylsilyldifluoride; iodine; sodium hydride; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; 2-methyl-propan-1-ol; water; dimethyl sulfoxide; acetone;
DOI:10.1002/chem.201102351