(2R,6S)-6-[(4S)-4-benzyloxy-3,3-dimethyl-2-oxohex-5-enyl]-4-methylene-2-[(2-trimethylsilylethoxy)methoxy]methyltetrahydropyran

Base Information

Chemical Name:(2R,6S)-6-[(4S)-4-benzyloxy-3,3-dimethyl-2-oxohex-5-enyl]-4-methylene-2-[(2-trimethylsilylethoxy)methoxy]methyltetrahydropyran
CAS No.:1314809-05-6
Molecular Formula:C₂₈H₄₄O₅Si
Molecular Weight:488.74
Hs Code.:

Synonyms:(2R,6S)-6-[(4S)-4-benzyloxy-3,3-dimethyl-2-oxohex-5-enyl]-4-methylene-2-[(2-trimethylsilylethoxy)methoxy]methyltetrahydropyran

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Chemical Property of (2R,6S)-6-[(4S)-4-benzyloxy-3,3-dimethyl-2-oxohex-5-enyl]-4-methylene-2-[(2-trimethylsilylethoxy)methoxy]methyltetrahydropyran

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Technology Process of (2R,6S)-6-[(4S)-4-benzyloxy-3,3-dimethyl-2-oxohex-5-enyl]-4-methylene-2-[(2-trimethylsilylethoxy)methoxy]methyltetrahydropyran

There total 10 articles about (2R,6S)-6-[(4S)-4-benzyloxy-3,3-dimethyl-2-oxohex-5-enyl]-4-methylene-2-[(2-trimethylsilylethoxy)methoxy]methyltetrahydropyran 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

: 76513-69-4
(2-trimethylethylsilylethoxy)methyl chloride

: 1314809-05-6
(2R,6S)-6-[(4S)-4-benzyloxy-3,3-dimethyl-2-oxohex-5-enyl]-4-methylene-2-[(2-trimethylsilylethoxy)methoxy]methyltetrahydropyran

: 1314809-07-8
(2R,6R)-6-[(4S)-4-benzyloxy-3,3-dimethyl-2-oxohex-5-enyl]-4-methylene-2-[(2-trimethylsilylethoxy)methoxy]methyltetrahydropyran

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 15h; 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

: 1314809-05-6
(2R,6S)-6-[(4S)-4-benzyloxy-3,3-dimethyl-2-oxohex-5-enyl]-4-methylene-2-[(2-trimethylsilylethoxy)methoxy]methyltetrahydropyran

: 1314809-07-8
(2R,6R)-6-[(4S)-4-benzyloxy-3,3-dimethyl-2-oxohex-5-enyl]-4-methylene-2-[(2-trimethylsilylethoxy)methoxy]methyltetrahydropyran

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: N-ethyl-N,N-diisopropylamine / dichloromethane / 15 h / 20 °C / Inert atmosphere

With oxalyl dichloride; hydrogen fluoride; water; Dess-Martin periodane; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; 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

: 1314809-05-6
(2R,6S)-6-[(4S)-4-benzyloxy-3,3-dimethyl-2-oxohex-5-enyl]-4-methylene-2-[(2-trimethylsilylethoxy)methoxy]methyltetrahydropyran

: 1314809-07-8
(2R,6R)-6-[(4S)-4-benzyloxy-3,3-dimethyl-2-oxohex-5-enyl]-4-methylene-2-[(2-trimethylsilylethoxy)methoxy]methyltetrahydropyran

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: N-ethyl-N,N-diisopropylamine / dichloromethane / 15 h / 20 °C / Inert atmosphere

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