2-((2S,3S)-3-{(R)-2-[(1R,3R,3aR,3bS,6R,6aR,6bR)-3-(4-Methoxy-benzyloxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-1-triethylsilanyloxy-allyl}-oxiranyl)-propan-2-ol

Base Information

• Chemical Name: 2-((2S,3S)-3-{(R)-2-[(1R,3R,3aR,3bS,6R,6aR,6bR)-3-(4-Methoxy-benzyloxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-1-triethylsilanyloxy-allyl}-oxiranyl)-propan-2-ol
• CAS No.: 127182-32-5
• Molecular Formula: C₃₄H₅₄O₅Si
• Molecular Weight: 570.885
• Mol file: 127182-32-5.mol

Synonyms:2-((2S,3S)-3-{(R)-2-[(1R,3R,3aR,3bS,6R,6aR,6bR)-3-(4-Methoxy-benzyloxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-1-triethylsilanyloxy-allyl}-oxiranyl)-propan-2-ol

Chemical Property of 2-((2S,3S)-3-{(R)-2-[(1R,3R,3aR,3bS,6R,6aR,6bR)-3-(4-Methoxy-benzyloxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-1-triethylsilanyloxy-allyl}-oxiranyl)-propan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-((2S,3S)-3-{(R)-2-[(1R,3R,3aR,3bS,6R,6aR,6bR)-3-(4-Methoxy-benzyloxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-1-triethylsilanyloxy-allyl}-oxiranyl)-propan-2-ol

There total 10 articles about 2-((2S,3S)-3-{(R)-2-[(1R,3R,3aR,3bS,6R,6aR,6bR)-3-(4-Methoxy-benzyloxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-1-triethylsilanyloxy-allyl}-oxiranyl)-propan-2-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:

(E)-(S)-6-[(1R,3R,3aR,3bS,6R,6aR,6bR)-3-(4-Methoxy-benzyloxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-2-methyl-5-triethylsilanyloxy-hepta-3,6-dien-2-ol (127135-71-1) → 2-((2R,3R)-3-{(R)-2-[(1R,3R,3aR,3bS,6R,6aR,6bR)-3-(4-Methoxy-benzyloxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-1-triethylsilanyloxy-allyl}-oxiranyl)-propan-2-ol (127135-73-3) + 2-((2S,3S)-3-{(R)-2-[(1R,3R,3aR,3bS,6R,6aR,6bR)-3-(4-Methoxy-benzyloxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-1-triethylsilanyloxy-allyl}-oxiranyl)-propan-2-ol (127182-32-5)

Guidance literature:

With tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium; In benzene; at 60 ℃; for 3h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/ja00008a044

Reference yield:

triethylsilyl chloride (994-30-9) → 2-((2S,3S)-3-{(R)-2-[(1R,3R,3aR,3bS,6R,6aR,6bR)-3-(4-Methoxy-benzyloxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-1-triethylsilanyloxy-allyl}-oxiranyl)-propan-2-ol (127182-32-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / Et₃N, 4-(dimethylamino)pyridine / CH₂Cl₂ / 4 h / Ambient temperature

2: t-BuOOH, VO(acac)2 / benzene / 3 h / 60 °C

With tert.-butylhydroperoxide; dmap; bis(acetylacetonate)oxovanadium; triethylamine; In dichloromethane; benzene;

DOI:10.1021/ja00008a044

Reference yield:

p-Methoxybenzyl bromide (2746-25-0) → 2-((2S,3S)-3-{(R)-2-[(1R,3R,3aR,3bS,6R,6aR,6bR)-3-(4-Methoxy-benzyloxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-1-triethylsilanyloxy-allyl}-oxiranyl)-propan-2-ol (127182-32-5)

Guidance literature:

Multi-step reaction with 7 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: t-BuOOH, VO(acac)2 / benzene / 3 h / 60 °C

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

DOI:10.1021/ja00008a044

upstream raw materials:

(E)-(S)-6-[(1R,3R,3aR,3bS,6R,6aR,6bR)-3-(4-Methoxy-benzyloxy)-3a,6-dimethyl-decahydro-cyclobutadicyclopenten-1-yl]-2-methyl-5-triethylsilanyloxy-hepta-3,6-dien-2-ol

triethylsilyl chloride

p-Methoxybenzyl bromide

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