(2R,3S,22S,24E)-6,6-(Ethylenedioxy)-2,3-(isopropylidenedioxy)-24-(phenylseleno)-25-(p-tolylsulfonyl)-(5α)-26,27-dinorcholest-24-en-22-ol

Base Information

Chemical Name:(2R,3S,22S,24E)-6,6-(Ethylenedioxy)-2,3-(isopropylidenedioxy)-24-(phenylseleno)-25-(p-tolylsulfonyl)-(5α)-26,27-dinorcholest-24-en-22-ol
CAS No.:130200-11-2
Molecular Formula:C₄₃H₅₈O₇SSe
Molecular Weight:797.955
Hs Code.:

Synonyms:(2R,3S,22S,24E)-6,6-(Ethylenedioxy)-2,3-(isopropylidenedioxy)-24-(phenylseleno)-25-(p-tolylsulfonyl)-(5α)-26,27-dinorcholest-24-en-22-ol

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Chemical Property of (2R,3S,22S,24E)-6,6-(Ethylenedioxy)-2,3-(isopropylidenedioxy)-24-(phenylseleno)-25-(p-tolylsulfonyl)-(5α)-26,27-dinorcholest-24-en-22-ol

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Technology Process of (2R,3S,22S,24E)-6,6-(Ethylenedioxy)-2,3-(isopropylidenedioxy)-24-(phenylseleno)-25-(p-tolylsulfonyl)-(5α)-26,27-dinorcholest-24-en-22-ol

There total 1 articles about (2R,3S,22S,24E)-6,6-(Ethylenedioxy)-2,3-(isopropylidenedioxy)-24-(phenylseleno)-25-(p-tolylsulfonyl)-(5α)-26,27-dinorcholest-24-en-22-ol 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:

: 6224-91-5
trimethyl(prop-1-ynyl)silane

: 68819-94-3
p-tolyl benzeneselenosulfonate

: 81481-15-4
(20S)-6,6-ethylenedioxy-2α,3α-isopropylidenedioxy-5α-pregnane-20-carbaldehyde

: 130200-10-1
(2R,3S,22R,24E)-6,6-(Ethylenedioxy)-2,3-(isopropylidenedioxy)-24-(phenylseleno)-25-(p-tolylsulfonyl)-(5α)-26,27-dinorcholest-24-en-22-ol

: 130200-11-2
(2R,3S,22S,24E)-6,6-(Ethylenedioxy)-2,3-(isopropylidenedioxy)-24-(phenylseleno)-25-(p-tolylsulfonyl)-(5α)-26,27-dinorcholest-24-en-22-ol

Guidance literature:: Yield given. Multistep reaction. Yields of byproduct given;
DOI:10.1021/jo00001a089

Reference yield: 66.0%

: 130200-11-2
(2R,3S,22S,24E)-6,6-(Ethylenedioxy)-2,3-(isopropylidenedioxy)-24-(phenylseleno)-25-(p-tolylsulfonyl)-(5α)-26,27-dinorcholest-24-en-22-ol

: 130200-12-3
(2R,3S,22R,23Z)-6,6-(Ethylenedioxy)-2,3-(isopropylidenedioxy)-24-(phenylseleno)-25-(p-tolylsulfonyl)-(5α)-26,27-dinorcholest-23-en-22-ol

Guidance literature:: With triethylamine; In toluene; for 48h; Heating;
DOI:10.1021/jo00001a089

Reference yield:

: 130200-11-2
(2R,3S,22S,24E)-6,6-(Ethylenedioxy)-2,3-(isopropylidenedioxy)-24-(phenylseleno)-25-(p-tolylsulfonyl)-(5α)-26,27-dinorcholest-24-en-22-ol

: 80736-41-0
castasterone

Guidance literature:: Multi-step reaction with 7 steps

1: 66 percent / Et₃N / toluene / 48 h / Heating

2: 81 percent / tert-butyl hydroperoxide / 2-methyl-propan-2-ol; CHCl₃ / 10 h

3: 31 percent / lithium (2-thienyl)cyanocuprate / tetrahydrofuran; petroleum ether / 0.5 h / -78 °C

4: 51 percent / Mg(turnings), MeOH / tetrahydrofuran / 4 h / Ambient temperature

5: 95 percent / MCPBA

6: 73 percent / LiBH₄, borane-THF / tetrahydrofuran / 12 h / 0 °C

7: 82 percent / 80percent aqu. AcOH / 0.5 h / 50 °C

With methanol; tert.-butylhydroperoxide; lithium borohydride; borane-THF; magnesium; acetic acid; thien-2-yl(cyano)copper lithium; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; chloroform; toluene; Petroleum ether; tert-butyl alcohol;
DOI:10.1021/jo00001a089