(3aS,9bS)-2,2-dimethyl-1-(3-phenylpropanoyl)-1,3a,4,9b-tetrahydro-2H-chromeno[4,3-d][1,3]oxazole

Base Information

• Chemical Name: (3aS,9bS)-2,2-dimethyl-1-(3-phenylpropanoyl)-1,3a,4,9b-tetrahydro-2H-chromeno[4,3-d][1,3]oxazole
• CAS No.: 342600-27-5
• Molecular Formula: C₂₁H₂₃NO₃
• Molecular Weight: 337.419

Synonyms:(3aS,9bS)-2,2-dimethyl-1-(3-phenylpropanoyl)-1,3a,4,9b-tetrahydro-2H-chromeno[4,3-d][1,3]oxazole

Chemical Property of (3aS,9bS)-2,2-dimethyl-1-(3-phenylpropanoyl)-1,3a,4,9b-tetrahydro-2H-chromeno[4,3-d][1,3]oxazole

Chemical Property:

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Technology Process of (3aS,9bS)-2,2-dimethyl-1-(3-phenylpropanoyl)-1,3a,4,9b-tetrahydro-2H-chromeno[4,3-d][1,3]oxazole

There total 4 articles about (3aS,9bS)-2,2-dimethyl-1-(3-phenylpropanoyl)-1,3a,4,9b-tetrahydro-2H-chromeno[4,3-d][1,3]oxazole 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:

2,2-dimethoxy-propane (77-76-9) + N-((3S,4S)-3-Hydroxy-chroman-4-yl)-3-phenyl-propionamide (342600-28-6) → (3aS,9bS)-2,2-dimethyl-1-(3-phenylpropanoyl)-1,3a,4,9b-tetrahydro-2H-chromeno[4,3-d][1,3]oxazole (342600-27-5)

Guidance literature:

2,2-dimethoxy-propane; N-((3S,4S)-3-Hydroxy-chroman-4-yl)-3-phenyl-propionamide; With water; toluene-4-sulfonic acid; In tetrahydrofuran; for 6h; Heating / reflux;

With sodium hydrogencarbonate; In tetrahydrofuran; water;

Reference yield:

2-Methoxypropene (116-11-0) + N-((3S,4S)-3-Hydroxy-chroman-4-yl)-3-phenyl-propionamide (342600-28-6) → (3aS,9bS)-2,2-dimethyl-1-(3-phenylpropanoyl)-1,3a,4,9b-tetrahydro-2H-chromeno[4,3-d][1,3]oxazole (342600-27-5)

Guidance literature:

With methanesulfonic acid; In tetrahydrofuran; at 35 - 60 ℃;

DOI:10.1016/j.tetasy.2003.09.023

Reference yield:

hydrocinnamic acid chloride (645-45-4) → (3aS,9bS)-2,2-dimethyl-1-(3-phenylpropanoyl)-1,3a,4,9b-tetrahydro-2H-chromeno[4,3-d][1,3]oxazole (342600-27-5)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / tetrahydrofuran / 20 - 45 °C

2: 180 g / methanesulfonic acid / tetrahydrofuran / 35 - 60 °C

With methanesulfonic acid; triethylamine; In tetrahydrofuran;

DOI:10.1016/j.tetasy.2003.09.023

upstream raw materials:

2-Methoxypropene

N-((3S,4S)-3-Hydroxy-chroman-4-yl)-3-phenyl-propionamide

hydrocinnamic acid chloride

cis-4-amino-3-chromanol

Downstream raw materials:

(3aS,9bS)-1-[(2S)-2-benzylpent-4-enoyl]-2,2-dimethyl-1,3a,4,9b-tetrahydro-2H-chromeno[4,3-d][1,3]oxazole

tert-butyl (3S)-4-{(2S,4R)-4-benzyl-5-[(3aS,9bS)-2,2-dimethyl-3a,9b-dihydro-2H-chromeno[4,3-d][1,3]oxazol-1(4H)-yl]-2-hydroxy-5-oxopentyl}-3-{[(2,2,2-trifluoroethyl)amino]carbonyl}piperazine-1-carboxylate

(2S)-1-((2S,4R)-4-benzyl-5-{[(3S,4S)-3-hydroxy-3,4-dihydro-2H-chromen-4-yl]amino}-2-hydroxy-5-oxopentyl)-N-(2,2,2-trifluoroethyl)piperazine-2-carboxamide

(3aS,9bS)-1-{(2R)-2-benzyl-3-[(2S)-oxiran-2-yl]propanoyl}-2,2-dimethyl-1,3a,4,9b-tetrahydro-2H-chromeno[4,3-d][1,3]oxazole

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