(+/-)-ceroplastol

Base Information

• Chemical Name: (+/-)-ceroplastol
• CAS No.: 111614-72-3
• Molecular Formula: C₂₅H₄₀O
• Molecular Weight: 356.592

Synonyms:

Chemical Property of (+/-)-ceroplastol

Chemical Property:

Purity/Quality:

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Technology Process of (+/-)-ceroplastol

There total 22 articles about (+/-)-ceroplastol 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: 55.0%

C38H60N2O3SSi → ceroplastol-I (18674-12-9,111614-72-3,146451-61-8)

Guidance literature:

With sodium cyanoborohydride; zinc(II) chloride; In methanol; at 90 ℃; for 3h;

DOI:10.1021/ja00058a011

Reference yield:

(E)-(S)-6-[(Z)-(3R,3aR,6aR,9aS,10aS)-6,10a-Dimethyl-9-methylene-1-(p-tolyl-hydrazono)-1,2,3,3a,4,6a,7,8,9,9a,10,10a-dodecahydro-dicyclopenta[a,d]cycloocten-3-yl]-2-methyl-hept-2-en-1-ol → (+/-)-ceroplastol (18674-12-9,111614-72-3,146451-61-8)

Guidance literature:

With sodium cyanoborohydride; zinc(II) chloride; In methanol; at 90 ℃; for 4h; Yield given;

DOI:10.1021/ja00189a070

Reference yield:

(3aR,9aS)-2,3,3a,4,5,6,9,9a-octahydro-9a-methylspiro<1H-cyclopentacyclooctene-1,2'-<1,3>dioxolane> → ceroplastol-I (18674-12-9,111614-72-3,146451-61-8)

Guidance literature:

Multi-step reaction with 11 steps

1: 9 percent / KH₂PO₄, SeO₂ / toluene / 3 h / Heating

2: 78 percent / diethyl ether; tetrahydrofuran / 1 h / -78 °C

3: 90 percent / KH / tetrahydrofuran; methanol / 5 h

4: KN(SiMe₃)2 / tetrahydrofuran; toluene / 0.5 h

5: tetrahydrofuran; diethyl ether / 0.67 h / -20 °C

6: 84 percent / p-toluenesulfonic acid / acetone; H₂O / 13 h

7: 1.) LiN(SiMe₃)2 / 1.) THF, -78 deg C, 40 min, 2.) THF, from -78 deg C to RT

8: Pd(OAc)2 / acetonitrile / 1.5 h / Ambient temperature

9: 1.) CuBr*Me₂S, HMPA, 2.) trimethylsilyl chloride / 1.) THF, -78 deg C, 10 min, 2.) THF, -78 deg C, 30 min

10: 88 percent / oxalic acid dihydrate / ethanol / 24 h / Ambient temperature

11: 55 percent / NaBH₃CN, ZnCl₂ / methanol / 3 h / 90 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; palladium diacetate; potassium dihydrogenphosphate; chloro-trimethyl-silane; selenium(IV) oxide; copper(I) bromide dimethylsulfide complex; oxalic acid; potassium hydride; potassium hexamethylsilazane; sodium cyanoborohydride; toluene-4-sulfonic acid; zinc(II) chloride; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; ethanol; water; acetone; toluene; acetonitrile;

DOI:10.1021/ja00058a011

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