(2R,6S)-2-(acetoxymethyl)-6-[(4S)-3,3-dimethyl-4-(4-methoxybenzyloxy)-2-oxohex-5-enyl]-4-methylidenetetrahydropyran

Base Information

Chemical Name:(2R,6S)-2-(acetoxymethyl)-6-[(4S)-3,3-dimethyl-4-(4-methoxybenzyloxy)-2-oxohex-5-enyl]-4-methylidenetetrahydropyran
CAS No.:1314808-99-5
Molecular Formula:C₂₅H₃₄O₆
Molecular Weight:430.541
Hs Code.:

Synonyms:(2R,6S)-2-(acetoxymethyl)-6-[(4S)-3,3-dimethyl-4-(4-methoxybenzyloxy)-2-oxohex-5-enyl]-4-methylidenetetrahydropyran

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Chemical Property of (2R,6S)-2-(acetoxymethyl)-6-[(4S)-3,3-dimethyl-4-(4-methoxybenzyloxy)-2-oxohex-5-enyl]-4-methylidenetetrahydropyran

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Technology Process of (2R,6S)-2-(acetoxymethyl)-6-[(4S)-3,3-dimethyl-4-(4-methoxybenzyloxy)-2-oxohex-5-enyl]-4-methylidenetetrahydropyran

There total 6 articles about (2R,6S)-2-(acetoxymethyl)-6-[(4S)-3,3-dimethyl-4-(4-methoxybenzyloxy)-2-oxohex-5-enyl]-4-methylidenetetrahydropyran 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:

: C₂₃H₃₂O₅

: 108-24-7
acetic anhydride

: 1314808-99-5
(2R,6S)-2-(acetoxymethyl)-6-[(4S)-3,3-dimethyl-4-(4-methoxybenzyloxy)-2-oxohex-5-enyl]-4-methylidenetetrahydropyran

: 1314809-01-2
(2R,6R)-2-(acetoxymethyl)-6-[(4S)-3,3-dimethyl-4-(4-methoxybenzyloxy)-2-oxohex-5-enyl]-4-methylenetetrahydropyran

Guidance literature:: With pyridine; In dichloromethane; at 20 ℃; for 18h; Inert atmosphere;
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

: 1314808-99-5
(2R,6S)-2-(acetoxymethyl)-6-[(4S)-3,3-dimethyl-4-(4-methoxybenzyloxy)-2-oxohex-5-enyl]-4-methylidenetetrahydropyran

: 1314809-01-2
(2R,6R)-2-(acetoxymethyl)-6-[(4S)-3,3-dimethyl-4-(4-methoxybenzyloxy)-2-oxohex-5-enyl]-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: pyridine / dichloromethane / 18 h / 20 °C / Inert atmosphere

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

Reference yield:

: (3RS,5S)-5-(4-methoxybenzyloxy)-4,4-dimethylhept-6-en-1-yn-3-ol

: 1314808-99-5
(2R,6S)-2-(acetoxymethyl)-6-[(4S)-3,3-dimethyl-4-(4-methoxybenzyloxy)-2-oxohex-5-enyl]-4-methylidenetetrahydropyran

: 1314809-01-2
(2R,6R)-2-(acetoxymethyl)-6-[(4S)-3,3-dimethyl-4-(4-methoxybenzyloxy)-2-oxohex-5-enyl]-4-methylenetetrahydropyran

Guidance literature:: Multi-step reaction with 4 steps

1: Dess-Martin periodane / dichloromethane / 3 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: pyridine / dichloromethane / 18 h / 20 °C / Inert atmosphere

With pyridine; hydrogen fluoride; water; Dess-Martin periodane; zinc(II) iodide; In dichloromethane; acetonitrile; 3: oxy-Michael reaction;
DOI:10.1016/j.tet.2011.03.113