(2S,3R)-1-(4-Methoxy-phenyl)-3-trimethylsilanyloxy-pent-4-en-2-ol

Base Information

• Chemical Name: (2S,3R)-1-(4-Methoxy-phenyl)-3-trimethylsilanyloxy-pent-4-en-2-ol
• CAS No.: 173266-46-1
• Molecular Formula: C₁₅H₂₄O₃Si
• Molecular Weight: 280.439
• Mol file: 173266-46-1.mol

Synonyms:(2S,3R)-1-(4-Methoxy-phenyl)-3-trimethylsilanyloxy-pent-4-en-2-ol

Chemical Property of (2S,3R)-1-(4-Methoxy-phenyl)-3-trimethylsilanyloxy-pent-4-en-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-1-(4-Methoxy-phenyl)-3-trimethylsilanyloxy-pent-4-en-2-ol

There total 1 articles about (2S,3R)-1-(4-Methoxy-phenyl)-3-trimethylsilanyloxy-pent-4-en-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:

(2S,3R)-1,2-epoxy-4-penten-3-ol (102490-00-6) → (2S,3R)-1-(4-Methoxy-phenyl)-3-trimethylsilanyloxy-pent-4-en-2-ol (173266-46-1)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N, DMAP / CH₂Cl₂

2: 85 percent / copper(I) iodide / tetrahydrofuran / -10 °C

With dmap; copper(l) iodide; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/0957-4166(95)00383-5

Reference yield: 94.0%

methanesulfonyl chloride (124-63-0) + (2S,3R)-1-(4-Methoxy-phenyl)-3-trimethylsilanyloxy-pent-4-en-2-ol (173266-46-1) → Methanesulfonic acid (1S,2R)-1-(4-methoxy-benzyl)-2-trimethylsilanyloxy-but-3-enyl ester (173266-56-3)

Guidance literature:

With pyridine; In dichloromethane; Ambient temperature;

DOI:10.1016/0957-4166(95)00383-5

Reference yield:

(2S,3R)-1-(4-Methoxy-phenyl)-3-trimethylsilanyloxy-pent-4-en-2-ol (173266-46-1) → (-)-anisomycin (22862-76-6)

Guidance literature:

Multi-step reaction with 10 steps

1: 94 percent / pyridine / CH₂Cl₂ / Ambient temperature

2: NaN₃ / dimethylformamide / 7 h / 80 °C

3: 2N aq. HCl / 0.5 h

4: 95 percent / OsO₄, K₃Fe(CN)6, K₂CO₃, DHQ-CLB, water / 2-methyl-propan-2-ol

5: 89 percent / imidazole / dimethylformamide / 0 °C

6: pyridine / CH₂Cl₂ / 2 h / Ambient temperature

7: pyridine / 4 h / Ambient temperature

8: 91 percent / n-Bu₄NF / tetrahydrofuran / 1 h / 0 °C

9: 90 percent / lithium bromide / acetic acid; tetrahydrofuran / 24 h / Ambient temperature

10: NaOAc / methanol / 10 h / Heating

With pyridine; 1H-imidazole; hydrogenchloride; osmium(VIII) oxide; sodium azide; tetrabutyl ammonium fluoride; water; sodium acetate; potassium carbonate; (1R)-((1S,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methyl 4-chlorobenzoate; lithium bromide; potassium hexacyanoferrate(III); In tetrahydrofuran; methanol; dichloromethane; acetic acid; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1016/0957-4166(95)00383-5

upstream raw materials:

(2S,3R)-1,2-epoxy-4-penten-3-ol

Downstream raw materials:

Methanesulfonic acid (1S,2R)-1-(4-methoxy-benzyl)-2-trimethylsilanyloxy-but-3-enyl ester

(-)-anisomycin

(3R,4R)-4-Azido-5-(4-methoxy-phenyl)-pent-1-en-3-ol

Acetic acid (1S,2R)-2-azido-3-(4-methoxy-phenyl)-1-(S)-oxiranyl-propyl ester