2-[(1R,2R,3R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(R)-4-phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-ethanol

Base Information

• Chemical Name: 2-[(1R,2R,3R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(R)-4-phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-ethanol
• CAS No.: 99612-14-3
• Molecular Formula: C₃₃H₅₄O₇Si
• Molecular Weight: 590.873

Synonyms:2-[(1R,2R,3R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(R)-4-phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-ethanol

Chemical Property of 2-[(1R,2R,3R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(R)-4-phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-ethanol

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(1R,2R,3R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(R)-4-phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-ethanol

There total 5 articles about 2-[(1R,2R,3R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(R)-4-phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-ethanol 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: 91.8%

[(1R,2R,3R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(R)-4-phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-acetic acid methyl ester (99612-13-2) → 2-[(1R,2R,3R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(R)-4-phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-ethanol (99612-14-3)

Guidance literature:

With diisobutylaluminium hydride; In toluene; for 2.5h; 0 deg C to r.t.;

DOI:10.1021/jo00068a023

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 2-[(1R,2R,3R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(R)-4-phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-ethanol (99612-14-3)

Guidance literature:

Multi-step reaction with 3 steps

1: imidazole / dimethylformamide / Ambient temperature

2: 68.3 percent / NaHCO₃ / dimethylformamide / 24 h / 40 - 43 °C

3: 91.8 percent / DIBALH / toluene / 2.5 h / 0 deg C to r.t.

With 1H-imidazole; diisobutylaluminium hydride; sodium hydrogencarbonate; In N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo00068a023

Reference yield:

(3aR,4R,5R,6aS)-Hexahydro-4-<(E)-(3R)-4-phenoxy-3-<(tetrahydro-2H-pyran-2-yl)oxy>-1-butenyl>-5-<(tetrahydro-2H-pyran-2-yl)oxy>-2H-cyclopentafuran-2-one (54347-99-8,63324-35-6,64550-46-5,87302-48-5,150577-45-0) → 2-[(1R,2R,3R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(R)-4-phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-ethanol (99612-14-3)

Guidance literature:

Multi-step reaction with 4 steps

1: aq. KOH / tetrahydrofuran / 1 h / Heating

2: imidazole / dimethylformamide / Ambient temperature

3: 68.3 percent / NaHCO₃ / dimethylformamide / 24 h / 40 - 43 °C

4: 91.8 percent / DIBALH / toluene / 2.5 h / 0 deg C to r.t.

With 1H-imidazole; potassium hydroxide; diisobutylaluminium hydride; sodium hydrogencarbonate; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo00068a023

upstream raw materials:

[(1R,2R,3R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(R)-4-phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-acetic acid methyl ester

tert-butyldimethylsilyl chloride

(3aR,4R,5R,6aS)-Hexahydro-4-<(E)-(3R)-4-phenoxy-3-<(tetrahydro-2H-pyran-2-yl)oxy>-1-butenyl>-5-<(tetrahydro-2H-pyran-2-yl)oxy>-2H-cyclopentafuran-2-one

[(1R,2R,3R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(R)-4-phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-acetic acid

Downstream raw materials:

[(1R,2R,3R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(R)-4-phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-acetaldehyde

(3S)-3-Bromo-4-<(1R,2R,3R,5S)-5-<(tert-butyldimethylsilyl)oxy>-2-<(E)-(3R)-4-phenoxy-3-<(tetrahydro-2H-pyran-2-yl)oxy>-1-butenyl>-3-<(tetrahydro-2H-pyran-2-yl)oxy>cyclopentyl>but-1-yne

(3S)-4-<(1R,2R,3R,5S)-5-<(tert-Butyldimethylsilyl)oxy>-2-<(E)-(3R)-4-phenoxy-3-<(tetrahydro-2H-pyran-2-yl)oxy>-1-butenyl>-3-<(tetrahydro-2H-pyran-2-yl)oxy>cyclopentyl>but-1-yn-3-ol

(3R)-4-<(1R,2R,3R,5S)-5-<(tert-Butyldimethylsilyl)oxy>-2-<(E)-(3R)-4-phenoxy-3-<(tetrahydro-2H-pyran-2-yl)oxy>-1-butenyl>-3-<(tetrahydro-2H-pyran-2-yl)oxy>cyclopentyl>but-1-yn-3-ol

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