(3S,3aS,5aR,6R,9bS)-3,5a,9-Trimethyl-6-phenylselanylmethyl-3a,4,5,5a,6,9b-hexahydro-3H-furo[2,3-f]isochromene-2,8-dione

Base Information

Chemical Name:(3S,3aS,5aR,6R,9bS)-3,5a,9-Trimethyl-6-phenylselanylmethyl-3a,4,5,5a,6,9b-hexahydro-3H-furo[2,3-f]isochromene-2,8-dione
CAS No.:207742-44-7
Molecular Formula:C₂₁H₂₄O₄Se
Molecular Weight:419.379
Hs Code.:

Synonyms:(3S,3aS,5aR,6R,9bS)-3,5a,9-Trimethyl-6-phenylselanylmethyl-3a,4,5,5a,6,9b-hexahydro-3H-furo[2,3-f]isochromene-2,8-dione

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Chemical Property of (3S,3aS,5aR,6R,9bS)-3,5a,9-Trimethyl-6-phenylselanylmethyl-3a,4,5,5a,6,9b-hexahydro-3H-furo[2,3-f]isochromene-2,8-dione

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Technology Process of (3S,3aS,5aR,6R,9bS)-3,5a,9-Trimethyl-6-phenylselanylmethyl-3a,4,5,5a,6,9b-hexahydro-3H-furo[2,3-f]isochromene-2,8-dione

There total 8 articles about (3S,3aS,5aR,6R,9bS)-3,5a,9-Trimethyl-6-phenylselanylmethyl-3a,4,5,5a,6,9b-hexahydro-3H-furo[2,3-f]isochromene-2,8-dione 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: 93.0%

: 5707-04-0
Phenylselenyl chloride

: 207742-42-5
2-[(3S,3aS,6S,7aS)-3,6-Dimethyl-2-oxo-6-vinyl-hexahydro-benzofuran-(7E)-ylidene]-propionic acid methyl ester

: 207742-44-7
(3S,3aS,5aR,6R,9bS)-3,5a,9-Trimethyl-6-phenylselanylmethyl-3a,4,5,5a,6,9b-hexahydro-3H-furo[2,3-f]isochromene-2,8-dione

Guidance literature:: In water; acetonitrile; for 2h; Ambient temperature;
DOI:10.1016/S0040-4039(98)00363-3

Reference yield:

: 481-06-1
santonin

: 207742-44-7
(3S,3aS,5aR,6R,9bS)-3,5a,9-Trimethyl-6-phenylselanylmethyl-3a,4,5,5a,6,9b-hexahydro-3H-furo[2,3-f]isochromene-2,8-dione

Guidance literature:: Multi-step reaction with 8 steps

1: 100 percent / hydrogen / Wilkinson catalyst / benzene

2: 65 percent / acetic acid / 20 h / 80 °C

3: 95 percent / p-toluenesulphonic acid / methanol / 5 h / Heating

4: methanol; hexane / 0.42 h / Ambient temperature

5: sodium borohydride / methanol / 0.42 h / 0 °C

6: 84 percent / Bu₃P / tetrahydrofuran; pyridine / 1 h / Ambient temperature

7: 89 percent / 30percent H₂O₂ / tetrahydrofuran / 7 h / 0 - 20 °C

8: 93 percent / acetonitrile; H₂O / 2 h / Ambient temperature

With sodium tetrahydroborate; tributylphosphine; hydrogen; dihydrogen peroxide; toluene-4-sulfonic acid; Wilkinson's catalyst; In tetrahydrofuran; pyridine; methanol; hexane; water; acetic acid; acetonitrile; benzene;
DOI:10.1016/S0040-4039(98)00363-3

Reference yield:

: 207742-41-4
2-[(3S,3aS,6S,7aS)-3,6-Dimethyl-6-[2-(2-nitro-phenylselanyl)-ethyl]-2-oxo-hexahydro-benzofuran-(7E)-ylidene]-propionic acid methyl ester

: 207742-44-7
(3S,3aS,5aR,6R,9bS)-3,5a,9-Trimethyl-6-phenylselanylmethyl-3a,4,5,5a,6,9b-hexahydro-3H-furo[2,3-f]isochromene-2,8-dione

Guidance literature:: Multi-step reaction with 2 steps

1: 89 percent / H₂O₂; water / tetrahydrofuran

2: 93 percent / acetonitrile; H₂O / 2 h / 20 °C

With water; dihydrogen peroxide; In tetrahydrofuran; water; acetonitrile; 1: Oxidation / 2: Cyclization;
DOI:10.1002/1099-0690(200006)2000:11<2145::AID-EJOC2145>3.0.CO;2-N