Benzoic acid (4R,6R)-2-oxy-6-((1S,2R)-2-phenyl-cyclohexyloxy)-5,6-dihydro-4H-[1,2]oxazin-4-yl ester

Base Information

• Chemical Name: Benzoic acid (4R,6R)-2-oxy-6-((1S,2R)-2-phenyl-cyclohexyloxy)-5,6-dihydro-4H-[1,2]oxazin-4-yl ester
• CAS No.: 158250-17-0
• Molecular Formula: C₂₃H₂₅NO₅
• Molecular Weight: 395.455

Synonyms:Benzoic acid (4R,6R)-2-oxy-6-((1S,2R)-2-phenyl-cyclohexyloxy)-5,6-dihydro-4H-[1,2]oxazin-4-yl ester

Chemical Property of Benzoic acid (4R,6R)-2-oxy-6-((1S,2R)-2-phenyl-cyclohexyloxy)-5,6-dihydro-4H-[1,2]oxazin-4-yl ester

Chemical Property:

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Technology Process of Benzoic acid (4R,6R)-2-oxy-6-((1S,2R)-2-phenyl-cyclohexyloxy)-5,6-dihydro-4H-[1,2]oxazin-4-yl ester

There total 2 articles about Benzoic acid (4R,6R)-2-oxy-6-((1S,2R)-2-phenyl-cyclohexyloxy)-5,6-dihydro-4H-[1,2]oxazin-4-yl ester 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: 71.0%

(+)-(1R,2S)-trans-phenylcyclohexanol vinyl ether + benzoic acid 2-nitrovinyl ester (118297-30-6) → Benzoic acid (4R,6R)-2-oxy-6-((1S,2R)-2-phenyl-cyclohexyloxy)-5,6-dihydro-4H-[1,2]oxazin-4-yl ester (158250-17-0)

Guidance literature:

With titanium(IV) dichlorodiisopropylate; In dichloromethane; 1.) -90 deg C, 10 min, 2.) -78 deg C, 4.5 h;

DOI:10.1021/jo00098a027

Reference yield:

benzoyl chloride (98-88-4) → Benzoic acid (4R,6R)-2-oxy-6-((1S,2R)-2-phenyl-cyclohexyloxy)-5,6-dihydro-4H-[1,2]oxazin-4-yl ester (158250-17-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / nitromethane / 2.25 h / -23 °C

2: 71 percent / Ti(O-i-Pr)2Cl₂ / CH₂Cl₂ / 1.) -90 deg C, 10 min, 2.) -78 deg C, 4.5 h

With titanium(IV) dichlorodiisopropylate; In nitromethane; dichloromethane;

DOI:10.1021/jo00098a027

Reference yield: 97.0%

Benzoic acid (4R,6R)-2-oxy-6-((1S,2R)-2-phenyl-cyclohexyloxy)-5,6-dihydro-4H-[1,2]oxazin-4-yl ester (158250-17-0) + (Z)-1-[(dimethyl(1,1,2-trimethylpropyl)silyl)oxy]-4-(dimethylphenylsilyl)-3-buten-2-one (212612-90-3) → (2S,3R,3aR,4R,6R)-4-(benzoyloxy)-2-{2-[dimethyl(1,1,2-trimethylpropyl)silyloxy]-1-oxoethyl}-3-(dimethylphenylsilyl)-6-[(1S,2R)-(2-phenylcyclohexyl)oxy]hexahydroisoxazolo[2,3-b][1,2]oxazine (212612-91-4)

Guidance literature:

In benzene; at 25 ℃;

DOI:10.1021/ja980705p

upstream raw materials:

benzoic acid 2-nitrovinyl ester

benzoyl chloride

Downstream raw materials:

(-)-(2S,3aS,3R,4R,6R)-3-Carbomethoxy-4-(benzoyloxy)-6-<(1S,2R)-2-phenyl-cyclohexyloxy>hexahydroisoxazolo<1,7-b> <1,2>oxazine-2-carboxylic acid methyl ester

(2S,3R,3aR,4R,6R)-4-(benzoyloxy)-2-{2-[dimethyl(1,1,2-trimethylpropyl)silyloxy]-1-oxoethyl}-3-(dimethylphenylsilyl)-6-[(1S,2R)-(2-phenylcyclohexyl)oxy]hexahydroisoxazolo[2,3-b][1,2]oxazine

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