2-[(1,1-dimethylpent-4-enyl)oxy]ethyl (3R,4R)-4-(benzyloxy)-3-hydroxypentanoate

Base Information

Chemical Name:2-[(1,1-dimethylpent-4-enyl)oxy]ethyl (3R,4R)-4-(benzyloxy)-3-hydroxypentanoate
CAS No.:620616-03-7
Molecular Formula:C₂₁H₃₂O₅
Molecular Weight:364.482
Hs Code.:

Synonyms:2-[(1,1-dimethylpent-4-enyl)oxy]ethyl (3R,4R)-4-(benzyloxy)-3-hydroxypentanoate

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Chemical Property of 2-[(1,1-dimethylpent-4-enyl)oxy]ethyl (3R,4R)-4-(benzyloxy)-3-hydroxypentanoate

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Technology Process of 2-[(1,1-dimethylpent-4-enyl)oxy]ethyl (3R,4R)-4-(benzyloxy)-3-hydroxypentanoate

There total 8 articles about 2-[(1,1-dimethylpent-4-enyl)oxy]ethyl (3R,4R)-4-(benzyloxy)-3-hydroxypentanoate 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: 81.0%

: 620616-01-5
2-[(1,1-dimethylpent-4-enyl)oxy]ethyl (3R,4R)-4-(benzyloxy)-3-{[(tert-butyl)dimethylsilyl]oxy}pentanoate

: 620616-03-7
2-[(1,1-dimethylpent-4-enyl)oxy]ethyl (3R,4R)-4-(benzyloxy)-3-hydroxypentanoate

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃;
DOI:10.1002/hlca.200390151

Reference yield:

: 20449-21-2
2-(but-3-en-1-yl)-2-methyl-1,3-dioxolane

: 620616-03-7
2-[(1,1-dimethylpent-4-enyl)oxy]ethyl (3R,4R)-4-(benzyloxy)-3-hydroxypentanoate

Guidance literature:: Multi-step reaction with 3 steps

1.1: heptane; CH₂Cl₂ / 4 h / 0 °C

1.2: 96 percent / Me₃Al / heptane; CH₂Cl₂ / 6 h / Heating

2.1: 83 percent / DMAP; Et₃N; 2,4,6-trichlorobenzoyl chloride / toluene / 0.17 h / 0 °C

3.1: 81 percent / Bu₄NF / tetrahydrofuran / 0 - 20 °C

With dmap; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; n-heptane; dichloromethane; toluene; 2.1: Yamaguchi activation;
DOI:10.1002/hlca.200390151

Reference yield:

: 53346-05-7,41954-96-5,81445-44-5,81445-45-6
(R)-2-benzyloxypropanal

: 620616-03-7
2-[(1,1-dimethylpent-4-enyl)oxy]ethyl (3R,4R)-4-(benzyloxy)-3-hydroxypentanoate

Guidance literature:: Multi-step reaction with 6 steps

1: 81 percent / SnCl₄ / CH₂Cl₂ / 2 h / -78 °C

2: 99 percent / 1H-imidazole; DMAP / dimethylformamide; toluene / 4.5 h / 40 °C

3: 93 percent / O₃; Ph₃P / CH₂Cl₂ / 1.5 h / -78 °C

4: 99 percent / 2-methylbut-2-ene; NaClO₂; NaH₂PO₄*H₂O / 2-methyl-propan-2-ol; H₂O / 0.5 h

5: 83 percent / DMAP; Et₃N; 2,4,6-trichlorobenzoyl chloride / toluene / 0.17 h / 0 °C

6: 81 percent / Bu₄NF / tetrahydrofuran / 0 - 20 °C

With 1H-imidazole; dmap; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; tin(IV) chloride; ozone; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 5: Yamaguchi activation;
DOI:10.1002/hlca.200390151