(2R,6S)-6-[(4S)-4-benzyloxy-3,3-dimethyl-2-oxohex-5-enyl]-2-[(tert-butyldiphenylsilyloxy)methyl]-4-methylenetetrahydropyran

Base Information

Chemical Name:(2R,6S)-6-[(4S)-4-benzyloxy-3,3-dimethyl-2-oxohex-5-enyl]-2-[(tert-butyldiphenylsilyloxy)methyl]-4-methylenetetrahydropyran
CAS No.:1314809-09-0
Molecular Formula:C₃₈H₄₈O₄Si
Molecular Weight:596.882
Hs Code.:

Synonyms:(2R,6S)-6-[(4S)-4-benzyloxy-3,3-dimethyl-2-oxohex-5-enyl]-2-[(tert-butyldiphenylsilyloxy)methyl]-4-methylenetetrahydropyran

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Chemical Property of (2R,6S)-6-[(4S)-4-benzyloxy-3,3-dimethyl-2-oxohex-5-enyl]-2-[(tert-butyldiphenylsilyloxy)methyl]-4-methylenetetrahydropyran

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Technology Process of (2R,6S)-6-[(4S)-4-benzyloxy-3,3-dimethyl-2-oxohex-5-enyl]-2-[(tert-butyldiphenylsilyloxy)methyl]-4-methylenetetrahydropyran

There total 10 articles about (2R,6S)-6-[(4S)-4-benzyloxy-3,3-dimethyl-2-oxohex-5-enyl]-2-[(tert-butyldiphenylsilyloxy)methyl]-4-methylenetetrahydropyran 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:

: C₂₂H₃₀O₄

: 58479-61-1
tert-butylchlorodiphenylsilane

: 1314809-10-3
(2R,6R)-6-[(4S)-4-benzyloxy-3,3-dimethyl-2-oxohex-5-enyl]-2-[(tert-butyldiphenylsilyloxy)methyl]-4-methylidenetetrahydropyran

: 1314809-09-0
(2R,6S)-6-[(4S)-4-benzyloxy-3,3-dimethyl-2-oxohex-5-enyl]-2-[(tert-butyldiphenylsilyloxy)methyl]-4-methylenetetrahydropyran

Guidance literature:: With 1H-imidazole; In dichloromethane; at 20 ℃; for 18h; Inert atmosphere;
DOI:10.1016/j.tet.2011.03.113

Reference yield:

: 147252-93-5
(3S)-3-(benzyloxy)-2,2-dimethyl-4-penten-1-ol

: 1314809-10-3
(2R,6R)-6-[(4S)-4-benzyloxy-3,3-dimethyl-2-oxohex-5-enyl]-2-[(tert-butyldiphenylsilyloxy)methyl]-4-methylidenetetrahydropyran

: 1314809-09-0
(2R,6S)-6-[(4S)-4-benzyloxy-3,3-dimethyl-2-oxohex-5-enyl]-2-[(tert-butyldiphenylsilyloxy)methyl]-4-methylenetetrahydropyran

Guidance literature:: Multi-step reaction with 6 steps

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

1.2: -78 - 20 °C / Inert atmosphere

2.1: tetrahydrofuran / 18 h / -78 - 20 °C / Inert atmosphere

3.1: Dess-Martin periodane / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

4.1: zinc(II) iodide / dichloromethane / 24 h / 20 °C / Inert atmosphere; Molecular sieve; Darkness

5.1: hydrogen fluoride; water / acetonitrile / 18 h / 20 °C

6.1: 1H-imidazole / dichloromethane / 18 h / 20 °C / Inert atmosphere

With 1H-imidazole; oxalyl dichloride; hydrogen fluoride; water; Dess-Martin periodane; dimethyl sulfoxide; zinc(II) iodide; In tetrahydrofuran; dichloromethane; acetonitrile; 5.1: oxy-Michael reaction;
DOI:10.1016/j.tet.2011.03.113

Reference yield:

: 1314808-90-6
(R)-1-[(2-trimethylsilylethoxy)methoxy]-4-(trimethylsilylmethyl)pent-4-en-2-ol

: 1314809-10-3
(2R,6R)-6-[(4S)-4-benzyloxy-3,3-dimethyl-2-oxohex-5-enyl]-2-[(tert-butyldiphenylsilyloxy)methyl]-4-methylidenetetrahydropyran

: 1314809-09-0
(2R,6S)-6-[(4S)-4-benzyloxy-3,3-dimethyl-2-oxohex-5-enyl]-2-[(tert-butyldiphenylsilyloxy)methyl]-4-methylenetetrahydropyran

Guidance literature:: Multi-step reaction with 4 steps

1: 2,6-dimethylpyridine / dichloromethane / 18 h / 0 - 20 °C / Inert atmosphere

2: zinc(II) iodide / dichloromethane / 24 h / 20 °C / Inert atmosphere; Molecular sieve; Darkness

3: hydrogen fluoride; water / acetonitrile / 18 h / 20 °C

4: 1H-imidazole / dichloromethane / 18 h / 20 °C / Inert atmosphere

With 1H-imidazole; 2,6-dimethylpyridine; hydrogen fluoride; water; zinc(II) iodide; In dichloromethane; acetonitrile; 3: oxy-Michael reaction;
DOI:10.1016/j.tet.2011.03.113