(3R,5aR,9R,9aS,9bS)-3,9-Dimethyl-3,9-bis-phenylselanyl-5a-vinyl-octahydro-furo[2,3-f]isochromene-2,8-dione

Base Information

Chemical Name:(3R,5aR,9R,9aS,9bS)-3,9-Dimethyl-3,9-bis-phenylselanyl-5a-vinyl-octahydro-furo[2,3-f]isochromene-2,8-dione
CAS No.:76338-18-6
Molecular Formula:C₂₇H₂₈O₄Se₂
Molecular Weight:574.437
Hs Code.:

Synonyms:

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Chemical Property of (3R,5aR,9R,9aS,9bS)-3,9-Dimethyl-3,9-bis-phenylselanyl-5a-vinyl-octahydro-furo[2,3-f]isochromene-2,8-dione

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Technology Process of (3R,5aR,9R,9aS,9bS)-3,9-Dimethyl-3,9-bis-phenylselanyl-5a-vinyl-octahydro-furo[2,3-f]isochromene-2,8-dione

There total 30 articles about (3R,5aR,9R,9aS,9bS)-3,9-Dimethyl-3,9-bis-phenylselanyl-5a-vinyl-octahydro-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:

: 13902-54-0,13902-55-1,13902-61-9,14794-68-4,14804-46-7,14804-47-8,14987-66-7,17956-11-5,18409-87-5,32638-47-4,84652-34-6,143521-75-9,143521-76-0
tetrahydrosantonin

: 76338-18-6,76375-88-7
(3R,5aR,9S,9aS,9bS)-3,9-Dimethyl-3,9-bis-phenylselanyl-5a-vinyl-octahydro-furo[2,3-f]isochromene-2,8-dione

Guidance literature:: Multi-step reaction with 13 steps

1: boron trifluoride etherate

2: tetramethylammonium acetate / various solvent(s) / 8 h / Heating

3: 100 percent / sodium borohydride / methanol; CH₂Cl₂ / 0.5 h / -15 - -10 °C

4: 78.5 percent / HgO, I₂ / benzene / 3 h / Heating

5: KOH / methanol

6: pyridinium chlorochromate / CH₂Cl₂ / 3 h / Ambient temperature

7: 26 percent / Zn / ZnI₂ or ZnCl₂ / acetic acid / Heating

8: pyridinium p-toluenesulfonate / methanol / 3 h / Heating

9: 1) O₃, CH₃OH + CH₂Cl₂, -78 deg C, 2) NaBH₄, -20 deg C

10: 72 percent / 10 percent HCl / methanol / Heating

11: (C₄H₉)3P

12: H₂O₂

13: 1) LDA, -78 deg C, THF, 2) -40 deg C, THF - HMPA

With hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; (C₄H₉)3P; tetramethyl ammonium acetate; dihydrogen peroxide; iodine; pyridinium p-toluenesulfonate; pyridinium chlorochromate; mercury(II) oxide; zinc; boron trifluoride diethyl etherate; zinc(II) iodide; zinc(II) chloride; In methanol; dichloromethane; acetic acid; benzene;
DOI:10.1016/S0040-4039(00)78702-8

Reference yield:

: 13902-54-0,13902-55-1,13902-61-9,14794-68-4,14804-46-7,14804-47-8,14987-66-7,17956-11-5,18409-87-5,32638-47-4,84652-34-6,143521-75-9,143521-76-0
tetrahydrosantonin

: 76338-18-6,76375-88-7
(3R,5aR,9R,9aS,9bS)-3,9-Dimethyl-3,9-bis-phenylselanyl-5a-vinyl-octahydro-furo[2,3-f]isochromene-2,8-dione

Guidance literature:: Multi-step reaction with 13 steps

1: boron trifluoride etherate

2: tetramethylammonium acetate / various solvent(s) / 8 h / Heating

3: 100 percent / sodium borohydride / methanol; CH₂Cl₂ / 0.5 h / -15 - -10 °C

4: 78.5 percent / HgO, I₂ / benzene / 3 h / Heating

5: KOH / methanol

6: pyridinium chlorochromate / CH₂Cl₂ / 3 h / Ambient temperature

7: 26 percent / Zn / ZnI₂ or ZnCl₂ / acetic acid / Heating

8: pyridinium p-toluenesulfonate / methanol / 3 h / Heating

9: 1) O₃, CH₃OH + CH₂Cl₂, -78 deg C, 2) NaBH₄, -20 deg C

10: 72 percent / 10 percent HCl / methanol / Heating

11: (C₄H₉)3P

12: H₂O₂

13: 1) LDA, -78 deg C, THF, 2) -40 deg C, THF - HMPA

With hydrogenchloride; potassium hydroxide; sodium tetrahydroborate; (C₄H₉)3P; tetramethyl ammonium acetate; dihydrogen peroxide; iodine; pyridinium p-toluenesulfonate; pyridinium chlorochromate; mercury(II) oxide; zinc; boron trifluoride diethyl etherate; zinc(II) iodide; zinc(II) chloride; In methanol; dichloromethane; acetic acid; benzene;
DOI:10.1016/S0040-4039(00)78702-8

Reference yield:

: 60390-20-7,70868-11-0,70868-13-2,70868-15-4
Acetic acid (3S,5aS,7S,8R,9S,9aS,9bS)-7-hydroxy-3,5a,9-trimethyl-2-oxo-dodecahydro-naphtho[1,2-b]furan-8-yl ester

: 76338-18-6,76375-88-7
(3R,5aR,9R,9aS,9bS)-3,9-Dimethyl-3,9-bis-phenylselanyl-5a-vinyl-octahydro-furo[2,3-f]isochromene-2,8-dione

Guidance literature:: Multi-step reaction with 10 steps

1: 78.5 percent / HgO, I₂ / benzene / 3 h / Heating

2: KOH / methanol

3: pyridinium chlorochromate / CH₂Cl₂ / 3 h / Ambient temperature

4: 26 percent / Zn / ZnI₂ or ZnCl₂ / acetic acid / Heating

5: pyridinium p-toluenesulfonate / methanol / 3 h / Heating

6: 1) O₃, CH₃OH + CH₂Cl₂, -78 deg C, 2) NaBH₄, -20 deg C

7: 72 percent / 10 percent HCl / methanol / Heating

8: (C₄H₉)3P

9: H₂O₂

10: 1) LDA, -78 deg C, THF, 2) -40 deg C, THF - HMPA

With hydrogenchloride; potassium hydroxide; (C₄H₉)3P; dihydrogen peroxide; iodine; pyridinium p-toluenesulfonate; pyridinium chlorochromate; mercury(II) oxide; zinc; zinc(II) iodide; zinc(II) chloride; In methanol; dichloromethane; acetic acid; benzene;
DOI:10.1016/S0040-4039(00)78702-8