(3S,4R,6E)-1,1-dibromo-3-[(4-methoxyphenyl)methoxy]-4-methyl-8-pivaloyloxy-1,6-octadiene

Base Information

Chemical Name:(3S,4R,6E)-1,1-dibromo-3-[(4-methoxyphenyl)methoxy]-4-methyl-8-pivaloyloxy-1,6-octadiene
CAS No.:377751-01-4
Molecular Formula:C₂₂H₃₀Br₂O₄
Molecular Weight:518.286
Hs Code.:

Synonyms:(3S,4R,6E)-1,1-dibromo-3-[(4-methoxyphenyl)methoxy]-4-methyl-8-pivaloyloxy-1,6-octadiene

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Chemical Property of (3S,4R,6E)-1,1-dibromo-3-[(4-methoxyphenyl)methoxy]-4-methyl-8-pivaloyloxy-1,6-octadiene

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Technology Process of (3S,4R,6E)-1,1-dibromo-3-[(4-methoxyphenyl)methoxy]-4-methyl-8-pivaloyloxy-1,6-octadiene

There total 11 articles about (3S,4R,6E)-1,1-dibromo-3-[(4-methoxyphenyl)methoxy]-4-methyl-8-pivaloyloxy-1,6-octadiene 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:

: 558-13-4
carbon tetrabromide

: 2,2-Dimethyl-propionic acid (E)-(5R,6S)-6-(4-methoxy-benzyloxy)-5-methyl-7-oxo-hept-2-enyl ester

: 377751-01-4
(3S,4R,6E)-1,1-dibromo-3-[(4-methoxyphenyl)methoxy]-4-methyl-8-pivaloyloxy-1,6-octadiene

Guidance literature:: With triphenylphosphine; In dichloromethane; at -78 ℃; for 1h;
DOI:10.1021/ol016449u

Reference yield:

: 88406-01-3
2,3-O-isopropylidene-1-C-<(1R)-1-methylprop-2-enyl>-D-erythro-glycerol

: 377751-01-4
(3S,4R,6E)-1,1-dibromo-3-[(4-methoxyphenyl)methoxy]-4-methyl-8-pivaloyloxy-1,6-octadiene

Guidance literature:: Multi-step reaction with 9 steps

1.1: NaH / dimethylformamide / 0.5 h / 0 °C

1.2: 93 percent / dimethylformamide / 2 h / 0 °C

2.1: BH₃*SMe₂ / tetrahydrofuran / 2 h

2.2: 77 percent / aq. H₂O₂; NaOH / tetrahydrofuran; ethanol / 3.5 h

3.1: (COCl)2; Et₃N; DMSO / CH₂Cl₂ / 0.5 h / 20 °C

4.1: 616 mg / benzene / 14 h / 20 °C

5.1: 97 percent / DIBALH / CH₂Cl₂; toluene / 1 h / -78 °C

6.1: 97 percent / Et₃N / pyridine / 2 h / 0 °C

7.1: 95 percent / aq. AcOH / tetrahydrofuran / 18 h / 40 °C

8.1: NaIO₄ / methanol; H₂O / 0.5 h / 0 °C

9.1: 302 mg / Ph₃P / CH₂Cl₂ / 1 h / -78 °C

With sodium periodate; oxalyl dichloride; dimethylsulfide borane complex; sodium hydride; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene; 3.1: Swern oxidation / 4.1: Wittig reaction / 9.1: Corey-Fuchs homologation;
DOI:10.1021/ol016449u

Reference yield:

: 3282-30-2
pivaloyl chloride

: 377751-01-4
(3S,4R,6E)-1,1-dibromo-3-[(4-methoxyphenyl)methoxy]-4-methyl-8-pivaloyloxy-1,6-octadiene

Guidance literature:: Multi-step reaction with 4 steps

1: 97 percent / Et₃N / pyridine / 2 h / 0 °C

2: 95 percent / aq. AcOH / tetrahydrofuran / 18 h / 40 °C

3: NaIO₄ / methanol; H₂O / 0.5 h / 0 °C

4: 302 mg / Ph₃P / CH₂Cl₂ / 1 h / -78 °C

With sodium periodate; acetic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; 4: Corey-Fuchs homologation;
DOI:10.1021/ol016449u