(5S,6R)-6-{3-[(tert-butyldiphenyl)oxy]propyl}-5-methyl-2-(pent-4-en-1-yl)tetrahydro-2H-pyran-2-ol

Base Information

Chemical Name:(5S,6R)-6-{3-[(tert-butyldiphenyl)oxy]propyl}-5-methyl-2-(pent-4-en-1-yl)tetrahydro-2H-pyran-2-ol
CAS No.:1340479-63-1
Molecular Formula:C₃₀H₄₄O₃Si
Molecular Weight:480.763
Hs Code.:

Synonyms:(5S,6R)-6-{3-[(tert-butyldiphenyl)oxy]propyl}-5-methyl-2-(pent-4-en-1-yl)tetrahydro-2H-pyran-2-ol

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Chemical Property of (5S,6R)-6-{3-[(tert-butyldiphenyl)oxy]propyl}-5-methyl-2-(pent-4-en-1-yl)tetrahydro-2H-pyran-2-ol

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Technology Process of (5S,6R)-6-{3-[(tert-butyldiphenyl)oxy]propyl}-5-methyl-2-(pent-4-en-1-yl)tetrahydro-2H-pyran-2-ol

There total 8 articles about (5S,6R)-6-{3-[(tert-butyldiphenyl)oxy]propyl}-5-methyl-2-(pent-4-en-1-yl)tetrahydro-2H-pyran-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: 93.0%

: 1340479-62-0
(5S,6R)-6-{3-[(tert-butyldiphenyl)oxy]propyl}-5-methyltetrahydro-2H-pyran-2-one

: 34164-50-6
4-penten-1-ylmagnesium bromide

: 1340479-72-2
(2R,3S)-2-{3-[(tert-butyldiphenyl)oxy]propyl}-3-methyl-6-(pent-4-en-1-yl)-3,4-dihydro-2H-pyran

: 1340479-63-1
(5S,6R)-6-{3-[(tert-butyldiphenyl)oxy]propyl}-5-methyl-2-(pent-4-en-1-yl)tetrahydro-2H-pyran-2-ol

Guidance literature:: In diethyl ether; cyclohexane; at -20 ℃; for 16h; Inert atmosphere;
DOI:10.1021/ol202483u

Reference yield:

: 130372-07-5
4-(tret-butyldiphenylsilyloxy)butan-1-ol

: 1340479-72-2
(2R,3S)-2-{3-[(tert-butyldiphenyl)oxy]propyl}-3-methyl-6-(pent-4-en-1-yl)-3,4-dihydro-2H-pyran

: 1340479-63-1
(5S,6R)-6-{3-[(tert-butyldiphenyl)oxy]propyl}-5-methyl-2-(pent-4-en-1-yl)tetrahydro-2H-pyran-2-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1 h / -78 °C / Inert atmosphere

1.2: 0.67 h / -78 °C / Inert atmosphere

2.1: C₄₀H₄₀O₄Ti / tetrahydrofuran; diethyl ether / 2.17 h / -78 - 0 °C / Inert atmosphere

2.2: 20 h / -78 - 20 °C / Inert atmosphere

2.3: 48 h / 20 °C / Inert atmosphere

3.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 2 h / 80 °C / Inert atmosphere; Microwave irradiation

4.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 2 h / 20 °C

5.1: camphor-10-sulfonic acid / dichloromethane / 2 h / 20 °C

6.1: diethyl ether; cyclohexane / 16 h / -20 °C / Inert atmosphere

With Hoveyda-Grubbs catalyst second generation; oxalyl dichloride; C₄₀H₄₀O₄Ti; palladium 10% on activated carbon; camphor-10-sulfonic acid; hydrogen; dimethyl sulfoxide; In tetrahydrofuran; diethyl ether; dichloromethane; cyclohexane; ethyl acetate;
DOI:10.1021/ol202483u

Reference yield:

: 1119-51-3
bromopentene

: 1340479-72-2
(2R,3S)-2-{3-[(tert-butyldiphenyl)oxy]propyl}-3-methyl-6-(pent-4-en-1-yl)-3,4-dihydro-2H-pyran

: 1340479-63-1
(5S,6R)-6-{3-[(tert-butyldiphenyl)oxy]propyl}-5-methyl-2-(pent-4-en-1-yl)tetrahydro-2H-pyran-2-ol

Guidance literature:: Multi-step reaction with 2 steps

1: iodine; magnesium / diethyl ether / 4.25 h / Inert atmosphere; Reflux

2: diethyl ether; cyclohexane / 16 h / -20 °C / Inert atmosphere

With iodine; magnesium; In diethyl ether; cyclohexane;
DOI:10.1021/ol202483u