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

Base Information

• Chemical Name: 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
• CAS No.: 132101-62-3
• Molecular Formula: C₃₃H₄₆O₇
• Molecular Weight: 554.724
• Mol file: 132101-62-3.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 11 articles about 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 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: 79.0%

tetramethylammonium levulinate + Methanesulfonic acid (R)-1-[(2R,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 (127135-74-4) → 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)

Guidance literature:

With sodium hydrogencarbonate; In 1,2-dimethoxyethane; at 85 - 90 ℃; for 7h;

DOI:10.1021/ja00008a044

Reference yield:

p-Methoxybenzyl bromide (2746-25-0) → 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)

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: 4-(dimethylamino)pyridine / CH₂Cl₂ / 5 h / 0 - 5 °C

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

With tert.-butylhydroperoxide; dmap; manganese(IV) oxide; n-butyllithium; bis(acetylacetonate)oxovanadium; tetrabutyl ammonium fluoride; sodium hydride; sodium hydrogencarbonate; triethylamine; In tetrahydrofuran; 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) → 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)

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: 4-(dimethylamino)pyridine / CH₂Cl₂ / 5 h / 0 - 5 °C

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

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

DOI:10.1021/ja00008a044

upstream raw materials:

Methanesulfonic acid (R)-1-[(2R,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

(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