(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

Base Information

• Chemical Name: (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
• CAS No.: 99612-17-6
• Molecular Formula: C₃₅H₅₄O₇Si
• Molecular Weight: 614.895

Synonyms:(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

Chemical Property of (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

Chemical Property:

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Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (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

There total 7 articles about (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 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: 37.6%

ethynylmagnesium chloride (65032-27-1) + [(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 (99612-16-5) → (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 (99612-17-6) + (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 (99631-09-1)

Guidance literature:

In tetrahydrofuran;

DOI:10.1021/jo00068a023

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (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 (99612-17-6)

Guidance literature:

Multi-step reaction with 5 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.

4: CrO₃, pyridine, Celite / CH₂Cl₂ / 1 h

5: 24.9 percent / tetrahydrofuran

With pyridine; 1H-imidazole; chromium(VI) oxide; Celite; diisobutylaluminium hydride; sodium hydrogencarbonate; In tetrahydrofuran; dichloromethane; 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) → (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 (99612-17-6)

Guidance literature:

Multi-step reaction with 6 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.

5: CrO₃, pyridine, Celite / CH₂Cl₂ / 1 h

6: 24.9 percent / tetrahydrofuran

With pyridine; 1H-imidazole; chromium(VI) oxide; potassium hydroxide; Celite; diisobutylaluminium hydride; sodium hydrogencarbonate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo00068a023

upstream raw materials:

ethynylmagnesium chloride

[(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

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

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