R(-)-menthyl-21-hydroxy-3,3-ethylenedioxy-24-nor-chol-14,20⁽²²⁾-dien-23-ate

Base Information

Chemical Name:R(-)-menthyl-21-hydroxy-3,3-ethylenedioxy-24-nor-chol-14,20⁽²²⁾-dien-23-ate
CAS No.:122378-84-1
Molecular Formula:C₃₅H₅₄O₅
Molecular Weight:554.811
Hs Code.:

R(-)-menthyl-21-hydroxy-3,3-ethylenedioxy-24-nor-chol-14,20<sup>(22)</sup>-dien-23-ate

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of R(-)-menthyl-21-hydroxy-3,3-ethylenedioxy-24-nor-chol-14,20⁽²²⁾-dien-23-ate

Chemical Property:

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Technology Process of R(-)-menthyl-21-hydroxy-3,3-ethylenedioxy-24-nor-chol-14,20⁽²²⁾-dien-23-ate

There total 12 articles about R(-)-menthyl-21-hydroxy-3,3-ethylenedioxy-24-nor-chol-14,20⁽²²⁾-dien-23-ate 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: 19.9%

: 26315-61-7
L-menthyl glyoxylate

: 122378-83-0
20-oxo-5β-pregn-14-ene-3-one-3,3-ethylene ketal

: 122378-68-1
5β-card-14,20(22)-dienolide-3-one-3,3-ethylene ketal

: 122378-84-1
R(-)-menthyl-21-hydroxy-3,3-ethylenedioxy-24-nor-chol-14,20⁽²²⁾-dien-23-ate

Guidance literature:: With sodium tetrahydroborate; potassium hydride; In tetrahydrofuran; Ambient temperature; 1.) 1 h; 2.) methanol, 30 min;
DOI:10.1139/v89-088

Reference yield:

: 1229-12-5
androstane-3,17-dione

: 122378-84-1
R(-)-menthyl-21-hydroxy-3,3-ethylenedioxy-24-nor-chol-14,20⁽²²⁾-dien-23-ate

Guidance literature:: Multi-step reaction with 11 steps

1: 76 percent / p-toluenesulfonic acid / benzene / 3 h / Heating

2: 91 percent / potassium tert-butoxide / tetrahydrofuran / 5 h / Heating

3: 75 percent / selenium dioxide, 70percent tert-butyl hyperoxide / CH₂Cl₂ / 5 h / Ambient temperature

4: 86 percent / 1.) oxalyl chloride, dimethyl sulfoxide; 2.) triethylamine / CH₂Cl₂ / 1.) -78 deg C, 15 min; 2.) -20 deg C, 3 h

5: 84 percent / 1.) n-butyllithium/hexamethyldisilazane; 2.) 2,3-dicyano-4,5-dichlorobenzoquinone / tetrahydrofuran / 1.) -40 deg C, 15 min; 2.) CH₃CN, rt., 1 h

6: 75 percent / benzene / 0.5 h / Ambient temperature

7: 0.4M cerium chloride hydrate, sodium borohydride / methanol / 0.5 h / Ambient temperature

8: 68.1 percent / dimethylaminopyridine / CH₂Cl₂ / 0.25 h

9: 79.1 percent / 1.) tetrakis(triphenylphosphine)palladium (O); 2.) sodium borohydride / tetrahydrofuran / Ambient temperature; 1.) 15 min; 2.) 2 h

10: 81 percent / 1M diisobutylaluminum hydride / benzene; hexane / 0.5 h / Ambient temperature

11: 19.9 percent / 1.) 30percent potassium hydride; 2.) sodium borohydride / tetrahydrofuran / Ambient temperature; 1.) 1 h; 2.) methanol, 30 min

With tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; selenium(IV) oxide; cerium(III) chloride; oxalyl dichloride; 2,3-dicyano-4,5-dichlorobenzoquinone; potassium tert-butylate; potassium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; methanol; hexane; dichloromethane; benzene;
DOI:10.1139/v89-088

Reference yield:

: 122378-70-5
17-methylene-5β-androstan-3-one-3,3-ethylene ketal

: 122378-84-1
R(-)-menthyl-21-hydroxy-3,3-ethylenedioxy-24-nor-chol-14,20⁽²²⁾-dien-23-ate

Guidance literature:: Multi-step reaction with 9 steps

1: 75 percent / selenium dioxide, 70percent tert-butyl hyperoxide / CH₂Cl₂ / 5 h / Ambient temperature

2: 86 percent / 1.) oxalyl chloride, dimethyl sulfoxide; 2.) triethylamine / CH₂Cl₂ / 1.) -78 deg C, 15 min; 2.) -20 deg C, 3 h

3: 84 percent / 1.) n-butyllithium/hexamethyldisilazane; 2.) 2,3-dicyano-4,5-dichlorobenzoquinone / tetrahydrofuran / 1.) -40 deg C, 15 min; 2.) CH₃CN, rt., 1 h

4: 75 percent / benzene / 0.5 h / Ambient temperature

5: 0.4M cerium chloride hydrate, sodium borohydride / methanol / 0.5 h / Ambient temperature

6: 68.1 percent / dimethylaminopyridine / CH₂Cl₂ / 0.25 h

7: 79.1 percent / 1.) tetrakis(triphenylphosphine)palladium (O); 2.) sodium borohydride / tetrahydrofuran / Ambient temperature; 1.) 15 min; 2.) 2 h

8: 81 percent / 1M diisobutylaluminum hydride / benzene; hexane / 0.5 h / Ambient temperature

9: 19.9 percent / 1.) 30percent potassium hydride; 2.) sodium borohydride / tetrahydrofuran / Ambient temperature; 1.) 1 h; 2.) methanol, 30 min

With tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; selenium(IV) oxide; cerium(III) chloride; oxalyl dichloride; 2,3-dicyano-4,5-dichlorobenzoquinone; potassium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; methanol; hexane; dichloromethane; benzene;
DOI:10.1139/v89-088