Spatol

Base Information

• Chemical Name: Spatol
• CAS No.: 76520-52-0
• Molecular Formula: C20H30O3
• Molecular Weight: 318.4504
• Mol file: 76520-52-0.mol

Synonyms:(1R,3R,3aR,3bR,4R,6aS,6bR)-3-[1-((2S,3S,2'R)-3',3'-Dimethyl-[2,2']bioxiranyl-3-yl)-vinyl]-4,6b-dimethyl-decahydro-cyclobutadicyclopenten-1-ol;

Chemical Property of Spatol

Chemical Property:

• PSA: 45.29000
• LogP: 3.16660

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Spatol

There total 20 articles about Spatol 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: 81.0%

(2R,2'R,3'S)-3'-{1-[(1R,3R,3aR,3bS,6R,6aR,6bR)-3-(4-Methoxy-benzyloxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-vinyl}-3,3-dimethyl-[2,2']bioxiranyl (127182-33-6) → (+)-spatol (76520-52-0)

Guidance literature:

With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1021/ja00008a044

Reference yield:

(1R,3R,3aR,3bR,4R,6aS,6bR)-3-[1-(tert-Butyl-dimethyl-silanyloxymethyl)-vinyl]-4,6b-dimethyl-decahydro-cyclobutadicyclopenten-1-ol (132101-59-8) → (+)-spatol (76520-52-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) NaH / 1.) DME, RT, 30 min, 2.) reflux, 18 h

2: 93 percent / n-Bu₄NF / tetrahydrofuran / 16 h / Ambient temperature

3: 94 percent / MnO₂ / CH₂Cl₂ / 24 h / Ambient temperature

4: 1.) n-BuLi / 1.) THF, hexane, a) -78 deg C, 2 h, b) -10 deg C, 1 h, 2.) -78 deg C to RT, 4 h

5: 100 percent / n-Bu₄NF / tetrahydrofuran / 20 h / Ambient temperature

6: 100 percent / Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 4 h / Ambient temperature

7: 1.) t-BuOOH, VO(acac)2, 2.) n-Bu₄NF / 1.) benzene, 60 deg C, 3 h, 2.) THF, RT, 16 h

8: 1.) methanesulfonic anhydride, 4-(dimethylamino)pyridine, pyridine, 2.) t-BuOK / 1.) CH₂Cl₂, 0 deg C, 3 h, 2.) t-BuOH, RT, 1 h

9: 81 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), H₂O / CH₂Cl₂ / 1 h / 0 °C

With pyridine; tert.-butylhydroperoxide; dmap; manganese(IV) oxide; n-butyllithium; bis(acetylacetonate)oxovanadium; potassium tert-butylate; tetrabutyl ammonium fluoride; water; sodium hydride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Methanesulfonic anhydride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja00008a044

Reference yield:

2-[(1R,3R,3aR,3bS,6R,6aR,6bR)-3-(4-Methoxy-benzyloxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-propenal (127156-24-5) → (+)-spatol (76520-52-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) n-BuLi / 1.) THF, hexane, a) -78 deg C, 2 h, b) -10 deg C, 1 h, 2.) -78 deg C to RT, 4 h

2: 100 percent / n-Bu₄NF / tetrahydrofuran / 20 h / Ambient temperature

3: 100 percent / Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 4 h / Ambient temperature

4: 1.) t-BuOOH, VO(acac)2, 2.) n-Bu₄NF / 1.) benzene, 60 deg C, 3 h, 2.) THF, RT, 16 h

5: 1.) methanesulfonic anhydride, 4-(dimethylamino)pyridine, pyridine, 2.) t-BuOK / 1.) CH₂Cl₂, 0 deg C, 3 h, 2.) t-BuOH, RT, 1 h

6: 81 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ), H₂O / CH₂Cl₂ / 1 h / 0 °C

With pyridine; tert.-butylhydroperoxide; dmap; n-butyllithium; bis(acetylacetonate)oxovanadium; potassium tert-butylate; tetrabutyl ammonium fluoride; water; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Methanesulfonic anhydride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja00008a044

upstream raw materials:

(2R,2'R,3'S)-3'-{1-[(1R,3R,3aR,3bS,6R,6aR,6bR)-3-(4-Methoxy-benzyloxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-vinyl}-3,3-dimethyl-[2,2']bioxiranyl

(1R,3R,3aR,3bR,4R,6aS,6bR)-3-[1-(tert-Butyl-dimethyl-silanyloxymethyl)-vinyl]-4,6b-dimethyl-decahydro-cyclobutadicyclopenten-1-ol

2-[(1R,3R,3aR,3bS,6R,6aR,6bR)-3-(4-Methoxy-benzyloxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-propenal

2-[(1R,3R,3aR,3bS,6R,6aR,6bR)-3-(4-Methoxy-benzyloxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-prop-2-en-1-ol

Downstream raw materials:

4-Bromo-benzoic acid (1R,3R,3aR,3bR,4R,6aS,6bR)-3-{1-[(2S,3S)-3-((R)-1-chloro-2-hydroxy-2-methyl-propyl)-oxiranyl]-vinyl}-4,6b-dimethyl-decahydro-cyclobutadicyclopenten-1-yl ester