(2R,3S,6S)-2-<(E,S)-7-(Benzoyloxy)-4-methyloct-3-enyl>tetrahydro-3,6-dimethyl-2H-pyran-3-ol

Base Information

Chemical Name:(2R,3S,6S)-2-<(E,S)-7-(Benzoyloxy)-4-methyloct-3-enyl>tetrahydro-3,6-dimethyl-2H-pyran-3-ol
CAS No.:116216-70-7
Molecular Formula:C₂₃H₃₄O₄
Molecular Weight:374.521
Hs Code.:

Synonyms:(2R,3S,6S)-2-<(E,S)-7-(Benzoyloxy)-4-methyloct-3-enyl>tetrahydro-3,6-dimethyl-2H-pyran-3-ol

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Chemical Property of (2R,3S,6S)-2-<(E,S)-7-(Benzoyloxy)-4-methyloct-3-enyl>tetrahydro-3,6-dimethyl-2H-pyran-3-ol

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Technology Process of (2R,3S,6S)-2-<(E,S)-7-(Benzoyloxy)-4-methyloct-3-enyl>tetrahydro-3,6-dimethyl-2H-pyran-3-ol

There total 8 articles about (2R,3S,6S)-2-<(E,S)-7-(Benzoyloxy)-4-methyloct-3-enyl>tetrahydro-3,6-dimethyl-2H-pyran-3-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:

: 128243-76-5,128300-88-9
Benzoic acid (E)-(S)-8-((S)-2,5-dimethyl-tetrahydro-furan-2-yl)-8-methanesulfonyloxy-1,4-dimethyl-oct-4-enyl ester

: 128300-89-0
(2S,3R,6S)-2-<(E,S)-7-(Benzoyloxy)-4-methyloct-3-enyl>tetrahydro-3,6-dimethyl-2H-pyran-3-ol

: 116216-70-7
(2R,3S,6S)-2-<(E,S)-7-(Benzoyloxy)-4-methyloct-3-enyl>tetrahydro-3,6-dimethyl-2H-pyran-3-ol

Guidance literature:: With silver carbonate; In water; acetone; at 50 ℃; for 16h; Yield given. Yields of byproduct given;
DOI:10.1021/jo00304a022

Reference yield:

: 32663-39-1
(2E,6E)-2,7-dimethylocta-2,6-diene-1,8-diol

: 116216-70-7
(2R,3S,6S)-2-<(E,S)-7-(Benzoyloxy)-4-methyloct-3-enyl>tetrahydro-3,6-dimethyl-2H-pyran-3-ol

Guidance literature:: Multi-step reaction with 7 steps

2: 71 percent / butyllithium, TMEDA / tetrahydrofuran / 5 h / -10 °C

3: metallic Na / tetrahydrofuran; butan-1-ol / 3 h / Heating

4: 38 percent / Et₃N / CH₂Cl₂ / 20 h / Ambient temperature

5: 86 percent / NaOAc, VO(acac)2, tert.-butyl hydroperoxide (TBHP) / 1) benzene, reflux, 16 h, 2) AcOH, room temp., 1 h

6: Et₃N / CH₂Cl₂ / 1 h / -10 °C

7: Ag₂CO₃ / H₂O; acetone / 16 h / 50 °C

With tert.-butylhydroperoxide; n-butyllithium; bis(acetylacetonate)oxovanadium; N,N,N,N,-tetramethylethylenediamine; sodium acetate; sodium; triethylamine; silver carbonate; In tetrahydrofuran; dichloromethane; water; acetone; butan-1-ol;
DOI:10.1021/jo00304a022

Reference yield:

: 128243-74-3
(2S,5E,9E,13S)-5,10-Dimethyltetradeca-5,9-diene-2,13-diol

: 116216-70-7
(2R,3S,6S)-2-<(E,S)-7-(Benzoyloxy)-4-methyloct-3-enyl>tetrahydro-3,6-dimethyl-2H-pyran-3-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 38 percent / Et₃N / CH₂Cl₂ / 20 h / Ambient temperature

2: 86 percent / NaOAc, VO(acac)2, tert.-butyl hydroperoxide (TBHP) / 1) benzene, reflux, 16 h, 2) AcOH, room temp., 1 h

3: Et₃N / CH₂Cl₂ / 1 h / -10 °C

4: Ag₂CO₃ / H₂O; acetone / 16 h / 50 °C

With tert.-butylhydroperoxide; bis(acetylacetonate)oxovanadium; sodium acetate; triethylamine; silver carbonate; In dichloromethane; water; acetone;
DOI:10.1021/jo00304a022