ethyl (2'R,4'R,5'R)-3-[5'-(2,6-dichlorobenzyloxymethyl)-4'-methyltetrahydrofuran-2'-yl]propanoate

Base Information

Chemical Name:ethyl (2'R,4'R,5'R)-3-[5'-(2,6-dichlorobenzyloxymethyl)-4'-methyltetrahydrofuran-2'-yl]propanoate
CAS No.:930795-16-7
Molecular Formula:C₁₈H₂₄Cl₂O₄
Molecular Weight:375.292
Hs Code.:

Synonyms:ethyl (2'R,4'R,5'R)-3-[5'-(2,6-dichlorobenzyloxymethyl)-4'-methyltetrahydrofuran-2'-yl]propanoate

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Chemical Property of ethyl (2'R,4'R,5'R)-3-[5'-(2,6-dichlorobenzyloxymethyl)-4'-methyltetrahydrofuran-2'-yl]propanoate

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Technology Process of ethyl (2'R,4'R,5'R)-3-[5'-(2,6-dichlorobenzyloxymethyl)-4'-methyltetrahydrofuran-2'-yl]propanoate

There total 9 articles about ethyl (2'R,4'R,5'R)-3-[5'-(2,6-dichlorobenzyloxymethyl)-4'-methyltetrahydrofuran-2'-yl]propanoate 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:

: 930795-15-6
diethyl (2'S,4'R,5'R)-2-[(5'-(2,6-dichlorobenzyloxymethyl)-4'-methyltetrahydrofuran-2'-yl)methyl]malonate

: 930795-16-7
ethyl (2'R,4'R,5'R)-3-[5'-(2,6-dichlorobenzyloxymethyl)-4'-methyltetrahydrofuran-2'-yl]propanoate

Guidance literature:: With lithium chloride; In water; dimethyl sulfoxide; at 160 ℃; for 7h;
DOI:10.1021/jo062396o

Reference yield:

: 930795-14-5
(2S,4R,5R)-2-iodomethyl-5-(2,6-dichlorobenzyloxymethyl)-4-methyltetrahydrofuran

: 930795-16-7
ethyl (2'R,4'R,5'R)-3-[5'-(2,6-dichlorobenzyloxymethyl)-4'-methyltetrahydrofuran-2'-yl]propanoate

Guidance literature:: Multi-step reaction with 2 steps

1.1: NaH / dimethylformamide / 0.5 h

1.2: dimethylformamide / 90 °C

2.1: LiCl / dimethylsulfoxide; H₂O / 7 h / 160 °C

With sodium hydride; lithium chloride; In water; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/jo062396o

Reference yield:

: 930795-46-3
(3R,4R)-4,5-bis(2,6-dichlorobenzyloxy)-3-methyl-pent-1-ene

: 930795-16-7
ethyl (2'R,4'R,5'R)-3-[5'-(2,6-dichlorobenzyloxymethyl)-4'-methyltetrahydrofuran-2'-yl]propanoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: BH₃*THF / tetrahydrofuran / 10 h / 20 °C

1.2: NaOH; aq. H₂O₂ / tetrahydrofuran / 20 °C

2.1: Dess-Martin periodinane / CH₂Cl₂ / 2 h / 0 - 20 °C

3.1: n-BuLi / tetrahydrofuran; hexane / 1 h / cooling

3.2: tetrahydrofuran; hexane / 1 h / 0 °C

4.1: iodine / acetonitrile / 3 h / -20 °C

5.1: NaH / dimethylformamide / 0.5 h

5.2: dimethylformamide / 90 °C

6.1: LiCl / dimethylsulfoxide; H₂O / 7 h / 160 °C

With n-butyllithium; borane-THF; iodine; sodium hydride; Dess-Martin periodane; lithium chloride; In tetrahydrofuran; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; 2.1: Dess-Martin oxidation / 3.2: Wittig olefination;
DOI:10.1021/jo062396o