(1S,2S,3R,4R)-4-(tert-butyldimethylsiloxy)-2,3-(isopropylidenedioxy)-1-phenylhex-5-en-1-ol

Base Information

Chemical Name:(1S,2S,3R,4R)-4-(tert-butyldimethylsiloxy)-2,3-(isopropylidenedioxy)-1-phenylhex-5-en-1-ol
CAS No.:1438391-69-5
Molecular Formula:C₂₁H₃₄O₄Si
Molecular Weight:378.584
Hs Code.:

Synonyms:(1S,2S,3R,4R)-4-(tert-butyldimethylsiloxy)-2,3-(isopropylidenedioxy)-1-phenylhex-5-en-1-ol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1S,2S,3R,4R)-4-(tert-butyldimethylsiloxy)-2,3-(isopropylidenedioxy)-1-phenylhex-5-en-1-ol

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Technology Process of (1S,2S,3R,4R)-4-(tert-butyldimethylsiloxy)-2,3-(isopropylidenedioxy)-1-phenylhex-5-en-1-ol

There total 5 articles about (1S,2S,3R,4R)-4-(tert-butyldimethylsiloxy)-2,3-(isopropylidenedioxy)-1-phenylhex-5-en-1-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: 71.0%

: 1438391-68-4
(2R,3R,4R)-4-(tert-butyldimethylsiloxy)-2,3-(isopropylidenedioxy)-1-phenylhex-5-en-1-one

: 1438391-69-5
(1S,2S,3R,4R)-4-(tert-butyldimethylsiloxy)-2,3-(isopropylidenedioxy)-1-phenylhex-5-en-1-ol

: 1438391-70-8
(1R,2S,3R,4R)-4-(tert-butyldimethylsiloxy)-2,3-(isopropylidenedioxy)-1-phenylhex-5-en-1-ol

Guidance literature:: With 3Ce⁽¹⁺⁾*3Cl^(1-)*7H₂O; In methanol; at -78 ℃; for 0.5h; Overall yield = 93 %; Overall yield = 0.3 g; Inert atmosphere;
DOI:10.1055/s-0032-1318303

Reference yield:

: 63126-29-4,74752-95-7
(4R,5R)-2,2,N,N,N',N'-hexamethyl-1,3-dioxolane-4,5-dicarboxamide

: 1438391-69-5
(1S,2S,3R,4R)-4-(tert-butyldimethylsiloxy)-2,3-(isopropylidenedioxy)-1-phenylhex-5-en-1-ol

Guidance literature:: Multi-step reaction with 5 steps

1: tetrahydrofuran / 0 h / -15 °C / Inert atmosphere

2: 3Ce⁽¹⁺⁾*3Cl^(1-)*7H₂O; sodium tetrahydroborate / methanol / -78 °C / Inert atmosphere

3: 1H-imidazole; dmap / dichloromethane / 6 h / Reflux; Inert atmosphere

4: tetrahydrofuran / 0 h / -15 - -10 °C / Inert atmosphere

5: 3Ce⁽¹⁺⁾*3Cl^(1-)*7H₂O / methanol / 0.5 h / -78 °C / Inert atmosphere

With 1H-imidazole; dmap; sodium tetrahydroborate; 3Ce⁽¹⁺⁾*3Cl^(1-)*7H₂O; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1055/s-0032-1318303

Reference yield:

: 1438391-61-7
(2R,3S,4R)-4-hydroxy-2,3-(isopropylidenedioxy)-N,N-dimethylhex-5-enamide

: 1438391-69-5
(1S,2S,3R,4R)-4-(tert-butyldimethylsiloxy)-2,3-(isopropylidenedioxy)-1-phenylhex-5-en-1-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 1H-imidazole; dmap / dichloromethane / 6 h / Reflux; Inert atmosphere

2: tetrahydrofuran / 0 h / -15 - -10 °C / Inert atmosphere

3: 3Ce⁽¹⁺⁾*3Cl^(1-)*7H₂O / methanol / 0.5 h / -78 °C / Inert atmosphere

With 1H-imidazole; dmap; 3Ce⁽¹⁺⁾*3Cl^(1-)*7H₂O; In tetrahydrofuran; methanol; dichloromethane;
DOI:10.1055/s-0032-1318303