(R)-6-((Z)-(S)-3-Benzyloxymethyl-1-methyl-pent-1-enyl)-5,6-dihydro-pyran-2-one

Base Information

Chemical Name:(R)-6-((Z)-(S)-3-Benzyloxymethyl-1-methyl-pent-1-enyl)-5,6-dihydro-pyran-2-one
CAS No.:616207-88-6
Molecular Formula:C₁₉H₂₄O₃
Molecular Weight:300.398
Hs Code.:

Synonyms:(R)-6-((Z)-(S)-3-Benzyloxymethyl-1-methyl-pent-1-enyl)-5,6-dihydro-pyran-2-one

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Chemical Property of (R)-6-((Z)-(S)-3-Benzyloxymethyl-1-methyl-pent-1-enyl)-5,6-dihydro-pyran-2-one

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Technology Process of (R)-6-((Z)-(S)-3-Benzyloxymethyl-1-methyl-pent-1-enyl)-5,6-dihydro-pyran-2-one

There total 9 articles about (R)-6-((Z)-(S)-3-Benzyloxymethyl-1-methyl-pent-1-enyl)-5,6-dihydro-pyran-2-one 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: 83.0%

: 616207-87-5
Acrylic acid (Z)-(1R,4S)-1-allyl-4-benzyloxymethyl-2-methyl-hex-2-enyl ester

: 616207-88-6
(R)-6-((Z)-(S)-3-Benzyloxymethyl-1-methyl-pent-1-enyl)-5,6-dihydro-pyran-2-one

Guidance literature:: Grubbs catalyst first generation; In dichloromethane; at 40 ℃; for 12h;
DOI:10.1016/j.tetlet.2003.08.023

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 616207-88-6
(R)-6-((Z)-(S)-3-Benzyloxymethyl-1-methyl-pent-1-enyl)-5,6-dihydro-pyran-2-one

Guidance literature:: Multi-step reaction with 9 steps

1: 80 percent / TiCl₄; Et₃N / CH₂Cl₂ / 1.5 h / 0 °C

2: 94 percent / LiBH₄ / methanol; tetrahydrofuran / 1 h / 23 °C

3: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0.75 h / -60 °C

4: NaH / tetrahydrofuran / 2 h / -78 - -20 °C

5: 96 percent / Dibal-H / CH₂Cl₂ / 1 h / -78 - -40 °C

6: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1.5 h / 23 °C

7: diethyl ether / 3 h / -80 °C

8: 77 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

9: 83 percent / Cl₂(Pcy)2Ru=CHPh / CH₂Cl₂ / 12 h / 40 °C

With lithium borohydride; oxalyl dichloride; titanium tetrachloride; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; Grubbs catalyst first generation; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 3: Swern oxidation / 4: Horner-Emmons reaction;
DOI:10.1016/j.tetlet.2003.08.023

Reference yield:

: 916501-75-2
2-<(benzyloxy)-methyl>butyraldehyde

: 616207-88-6
(R)-6-((Z)-(S)-3-Benzyloxymethyl-1-methyl-pent-1-enyl)-5,6-dihydro-pyran-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: NaH / tetrahydrofuran / 2 h / -78 - -20 °C

2: 96 percent / Dibal-H / CH₂Cl₂ / 1 h / -78 - -40 °C

3: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1.5 h / 23 °C

4: diethyl ether / 3 h / -80 °C

5: 77 percent / Et₃N / CH₂Cl₂ / 2 h / 0 °C

6: 83 percent / Cl₂(Pcy)2Ru=CHPh / CH₂Cl₂ / 12 h / 40 °C

With sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; triethylamine; Grubbs catalyst first generation; In tetrahydrofuran; diethyl ether; dichloromethane; 1: Horner-Emmons reaction;
DOI:10.1016/j.tetlet.2003.08.023