(2S,3aS,8aR)-2-(2-Benzyloxy-ethyl)-hexahydro-furo[3,2-b]oxepin-5-one

Base Information

Chemical Name:(2S,3aS,8aR)-2-(2-Benzyloxy-ethyl)-hexahydro-furo[3,2-b]oxepin-5-one
CAS No.:850656-42-7
Molecular Formula:C₁₇H₂₂O₄
Molecular Weight:290.359
Hs Code.:

Synonyms:(2S,3aS,8aR)-2-(2-Benzyloxy-ethyl)-hexahydro-furo[3,2-b]oxepin-5-one

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Chemical Property of (2S,3aS,8aR)-2-(2-Benzyloxy-ethyl)-hexahydro-furo[3,2-b]oxepin-5-one

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Technology Process of (2S,3aS,8aR)-2-(2-Benzyloxy-ethyl)-hexahydro-furo[3,2-b]oxepin-5-one

There total 10 articles about (2S,3aS,8aR)-2-(2-Benzyloxy-ethyl)-hexahydro-furo[3,2-b]oxepin-5-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:

: 850656-95-0
4-[(2R,3S,5S)-5-(2-Benzyloxy-ethyl)-3-hydroxy-tetrahydro-furan-2-yl]-butyric acid

: 850656-42-7
(2S,3aS,8aR)-2-(2-Benzyloxy-ethyl)-hexahydro-furo[3,2-b]oxepin-5-one

Guidance literature:: 4-[(2R,3S,5S)-5-(2-Benzyloxy-ethyl)-3-hydroxy-tetrahydro-furan-2-yl]-butyric acid; With 2,4,6-trichlorobenzoyl chloride; triethylamine; In tetrahydrofuran; at 20 ℃; for 1.5h;

With dmap; In tetrahydrofuran; toluene; for 0.5h; Heating;
DOI:10.1021/ja042686r

Reference yield:

: 850656-94-9
(2S,3S,5S)-5-(2-Benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-carbaldehyde

: 850656-42-7
(2S,3aS,8aR)-2-(2-Benzyloxy-ethyl)-hexahydro-furo[3,2-b]oxepin-5-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: NaHMDS / tetrahydrofuran / 0.33 h / 0 °C

1.2: 209.1 mg / tetrahydrofuran / 1 h / 0 °C

2.1: 99 percent / H₂ / Pd/C / ethyl acetate; methanol / 5 h / 20 °C

3.1: aq. HCl / tetrahydrofuran / 5 h / 40 - 60 °C

4.1: aq. NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 0.75 h / 20 °C

5.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 1.5 h / 20 °C

5.2: 1.95 g / DMAP / tetrahydrofuran; toluene / 0.5 h / Heating

With hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; 2,4,6-trichlorobenzoyl chloride; hydrogen; sodium hexamethyldisilazane; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethyl acetate; tert-butyl alcohol; 1.2: Wittig reaction;
DOI:10.1021/ja042686r

Reference yield:

: 850656-40-5
[(2R,3S,5S)-5-(2-Benzyloxy-ethyl)-3-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-methanol

: 850656-42-7
(2S,3aS,8aR)-2-(2-Benzyloxy-ethyl)-hexahydro-furo[3,2-b]oxepin-5-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: SO₃*pyridine; Et₃N; DMSO / CH₂Cl₂ / 1.25 h / 0 °C

2.1: NaHMDS / tetrahydrofuran / 0.33 h / 0 °C

2.2: 209.1 mg / tetrahydrofuran / 1 h / 0 °C

3.1: 99 percent / H₂ / Pd/C / ethyl acetate; methanol / 5 h / 20 °C

4.1: aq. HCl / tetrahydrofuran / 5 h / 40 - 60 °C

5.1: aq. NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 0.75 h / 20 °C

6.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 1.5 h / 20 °C

6.2: 1.95 g / DMAP / tetrahydrofuran; toluene / 0.5 h / Heating

With hydrogenchloride; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; pyridine-SO₃ complex; 2,4,6-trichlorobenzoyl chloride; hydrogen; sodium hexamethyldisilazane; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; tert-butyl alcohol; 1.1: Swern oxidation / 2.2: Wittig reaction;
DOI:10.1021/ja042686r