(3β,20S,22E,24S)-24-(phenylsulfinyl)-3-<(tetrahydro-2H-pyran-2-yl)oxy>cholesta-5,22-dien-20-ol

Base Information

Chemical Name:(3β,20S,22E,24S)-24-(phenylsulfinyl)-3-<(tetrahydro-2H-pyran-2-yl)oxy>cholesta-5,22-dien-20-ol
CAS No.:79409-84-0
Molecular Formula:C₃₈H₅₆O₄S
Molecular Weight:608.926
Hs Code.:

Synonyms:(3β,20S,22E,24S)-24-(phenylsulfinyl)-3-<(tetrahydro-2H-pyran-2-yl)oxy>cholesta-5,22-dien-20-ol

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Chemical Property of (3β,20S,22E,24S)-24-(phenylsulfinyl)-3-<(tetrahydro-2H-pyran-2-yl)oxy>cholesta-5,22-dien-20-ol

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Technology Process of (3β,20S,22E,24S)-24-(phenylsulfinyl)-3-<(tetrahydro-2H-pyran-2-yl)oxy>cholesta-5,22-dien-20-ol

There total 5 articles about (3β,20S,22E,24S)-24-(phenylsulfinyl)-3-<(tetrahydro-2H-pyran-2-yl)oxy>cholesta-5,22-dien-20-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: 57.0%

: 79409-83-9
(3β,20S,22E,24S)-24-(phenylthio)-3-<(tetrahydro-2H-pyran-2-yl)oxy>cholesta-5,22-dien-20-ol

: 79409-85-1
(Z)-(S)-5-Benzenesulfinyl-2-[(3S,8S,9S,10R,13S,14S,17S)-10,13-dimethyl-3-(tetrahydro-pyran-2-yloxy)-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methyl-hept-4-en-2-ol

: 79409-84-0
(3β,20S,22E,24S)-24-(phenylsulfinyl)-3-<(tetrahydro-2H-pyran-2-yl)oxy>cholesta-5,22-dien-20-ol

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃; for 4h;
DOI:10.1021/jo00338a024

Reference yield:

: 5296-64-0
allyl phenyl thioether

: 79409-84-0
(3β,20S,22E,24S)-24-(phenylsulfinyl)-3-<(tetrahydro-2H-pyran-2-yl)oxy>cholesta-5,22-dien-20-ol

Guidance literature:: Multi-step reaction with 5 steps

1: 1) sBuLi / 1) THF, cyclohexane, -78 deg C, 3 h, 2) -78 deg C, 1.5 h

2: 1) sBuLi, hexamethylphosphoramide / 1) THF, cyclohexane, -78 deg C, 2.5 h, 2) -78 deg C, 3.0 h

3: 1) sBuLi, hexamethylphosphoramide / 1) THF, cyclohexane, -78 deg C, 2,5 h, 2) THF, cyclohexane, a) -78 deg C, 3 h, b) 25 deg C, 1.5 h

4: 85 percent / KF, 18-crown-6 / methanol / 13 h / Heating

5: 57 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 4 h / 0 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; potassium fluoride; 18-crown-6 ether; sec.-butyllithium; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane;
DOI:10.1021/jo00338a024

Reference yield:

: 78905-13-2
phenyl 1-(trimethylsilyl)prop-2-en-1-yl sulfide

: 79409-84-0
(3β,20S,22E,24S)-24-(phenylsulfinyl)-3-<(tetrahydro-2H-pyran-2-yl)oxy>cholesta-5,22-dien-20-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 1) sBuLi, hexamethylphosphoramide / 1) THF, cyclohexane, -78 deg C, 2.5 h, 2) -78 deg C, 3.0 h

2: 1) sBuLi, hexamethylphosphoramide / 1) THF, cyclohexane, -78 deg C, 2,5 h, 2) THF, cyclohexane, a) -78 deg C, 3 h, b) 25 deg C, 1.5 h

3: 85 percent / KF, 18-crown-6 / methanol / 13 h / Heating

4: 57 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 4 h / 0 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; potassium fluoride; 18-crown-6 ether; sec.-butyllithium; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane;
DOI:10.1021/jo00338a024