(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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Chemical Name:(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
CAS No.:342600-31-1
Molecular Formula:C₂₄H₂₇NO₄
Molecular Weight:393.483
Hs Code.:

Synonyms:(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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Chemical Property of (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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Technology Process of (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

There total 5 articles about (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 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: 81.0%

: 342600-30-0
(2S,3R)-4-benzyl-5-[(3aS,9bS)-2,2-dimethyl-3a,9b-dihydro-2H-chromeno[4,3-d][1,3]oxazol-1(4H)-yl]-1-iodo-5-oxopentan-2-ol

: 342600-31-1
(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

Guidance literature:: With sodium methylate; In methanol; Isopropyl acetate; at 15 ℃; for 1h;
DOI:10.1016/j.tetasy.2003.09.023

Reference yield:

: 645-45-4
hydrocinnamic acid chloride

: 342600-31-1
(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

Guidance literature:: Multi-step reaction with 4 steps

1.1: triethylamine / tetrahydrofuran / 20 - 45 °C

2.1: 180 g / methanesulfonic acid / tetrahydrofuran / 35 - 60 °C

3.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 2 h / -45 °C

3.2: 64.0 g / N-chlorosuccinimide; NaHCO₃; NaI / H₂O; isopropyl acetate / 5 - 30 °C

4.1: 81 percent / NaOMe / isopropyl acetate; methanol / 1 h / 15 °C

With methanesulfonic acid; sodium methylate; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; Isopropyl acetate;
DOI:10.1016/j.tetasy.2003.09.023

Reference yield:

: 342600-28-6
N-((3S,4S)-3-Hydroxy-chroman-4-yl)-3-phenyl-propionamide

: 342600-31-1
(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

Guidance literature:: Multi-step reaction with 3 steps

1.1: 180 g / methanesulfonic acid / tetrahydrofuran / 35 - 60 °C

2.1: lithium bis(trimethylsilyl)amide / tetrahydrofuran / 2 h / -45 °C

2.2: 64.0 g / N-chlorosuccinimide; NaHCO₃; NaI / H₂O; isopropyl acetate / 5 - 30 °C

3.1: 81 percent / NaOMe / isopropyl acetate; methanol / 1 h / 15 °C

With methanesulfonic acid; sodium methylate; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; Isopropyl acetate;
DOI:10.1016/j.tetasy.2003.09.023