(S)-1-[(2S,3R)-3-(1-Hydroxy-1-methyl-ethyl)-oxiranyl]-2-[(1R,3R,3aR,3bS,6R,6aR,6bR)-3-(4-methoxy-benzyloxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-prop-2-en-1-ol

Base Information

• Chemical Name: (S)-1-[(2S,3R)-3-(1-Hydroxy-1-methyl-ethyl)-oxiranyl]-2-[(1R,3R,3aR,3bS,6R,6aR,6bR)-3-(4-methoxy-benzyloxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-prop-2-en-1-ol
• CAS No.: 132199-68-9
• Molecular Formula: C₂₈H₄₀O₅
• Molecular Weight: 456.623
• Mol file: 132199-68-9.mol

Synonyms:(S)-1-[(2S,3R)-3-(1-Hydroxy-1-methyl-ethyl)-oxiranyl]-2-[(1R,3R,3aR,3bS,6R,6aR,6bR)-3-(4-methoxy-benzyloxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-prop-2-en-1-ol

Chemical Property of (S)-1-[(2S,3R)-3-(1-Hydroxy-1-methyl-ethyl)-oxiranyl]-2-[(1R,3R,3aR,3bS,6R,6aR,6bR)-3-(4-methoxy-benzyloxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-prop-2-en-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-[(2S,3R)-3-(1-Hydroxy-1-methyl-ethyl)-oxiranyl]-2-[(1R,3R,3aR,3bS,6R,6aR,6bR)-3-(4-methoxy-benzyloxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-prop-2-en-1-ol

There total 12 articles about (S)-1-[(2S,3R)-3-(1-Hydroxy-1-methyl-ethyl)-oxiranyl]-2-[(1R,3R,3aR,3bS,6R,6aR,6bR)-3-(4-methoxy-benzyloxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-prop-2-en-1-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: 88.0%

4-Oxo-pentanoic acid (S)-1-[(2S,3R)-3-(1-hydroxy-1-methyl-ethyl)-oxiranyl]-2-[(1R,3R,3aR,3bS,6R,6aR,6bR)-3-(4-methoxy-benzyloxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-allyl ester (132101-62-3) → (S)-1-[(2S,3R)-3-(1-Hydroxy-1-methyl-ethyl)-oxiranyl]-2-[(1R,3R,3aR,3bS,6R,6aR,6bR)-3-(4-methoxy-benzyloxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-prop-2-en-1-ol (132199-68-9)

Guidance literature:

With sodium tetrahydroborate; water; In 1,4-dioxane; for 3h; Ambient temperature;

DOI:10.1021/ja00008a044

Reference yield:

p-Methoxybenzyl bromide (2746-25-0) → (S)-1-[(2S,3R)-3-(1-Hydroxy-1-methyl-ethyl)-oxiranyl]-2-[(1R,3R,3aR,3bS,6R,6aR,6bR)-3-(4-methoxy-benzyloxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-prop-2-en-1-ol (132199-68-9)

Guidance literature:

Multi-step reaction with 10 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: 4-(dimethylamino)pyridine / CH₂Cl₂ / 5 h / 0 - 5 °C

9: 79 percent / NaHCO₃ / 1,2-dimethoxy-ethane / 7 h / 85 - 90 °C

10: 88 percent / NaBH₄, H₂O / dioxane / 3 h / Ambient temperature

With tert.-butylhydroperoxide; dmap; manganese(IV) oxide; sodium tetrahydroborate; n-butyllithium; bis(acetylacetonate)oxovanadium; tetrabutyl ammonium fluoride; water; sodium hydride; sodium hydrogencarbonate; triethylamine; In tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; dichloromethane;

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) → (S)-1-[(2S,3R)-3-(1-Hydroxy-1-methyl-ethyl)-oxiranyl]-2-[(1R,3R,3aR,3bS,6R,6aR,6bR)-3-(4-methoxy-benzyloxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-prop-2-en-1-ol (132199-68-9)

Guidance literature:

Multi-step reaction with 10 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: 4-(dimethylamino)pyridine / CH₂Cl₂ / 5 h / 0 - 5 °C

9: 79 percent / NaHCO₃ / 1,2-dimethoxy-ethane / 7 h / 85 - 90 °C

10: 88 percent / NaBH₄, H₂O / dioxane / 3 h / Ambient temperature

With tert.-butylhydroperoxide; dmap; manganese(IV) oxide; sodium tetrahydroborate; n-butyllithium; bis(acetylacetonate)oxovanadium; tetrabutyl ammonium fluoride; water; sodium hydride; sodium hydrogencarbonate; triethylamine; In tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; dichloromethane;

DOI:10.1021/ja00008a044

upstream raw materials:

4-Oxo-pentanoic acid (S)-1-[(2S,3R)-3-(1-hydroxy-1-methyl-ethyl)-oxiranyl]-2-[(1R,3R,3aR,3bS,6R,6aR,6bR)-3-(4-methoxy-benzyloxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-allyl ester

p-Methoxybenzyl bromide

(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

Downstream raw materials:

(2S,2'S,3'R)-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