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

Base Information

Chemical Name:diethyl (2'S,4'R,5'R)-2-[(5'-(2,6-dichlorobenzyloxymethyl)-4'-methyltetrahydrofuran-2'-yl)methyl]malonate
CAS No.:930795-15-6
Molecular Formula:C₂₁H₂₈Cl₂O₆
Molecular Weight:447.356
Hs Code.:

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

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Chemical Property of diethyl (2'S,4'R,5'R)-2-[(5'-(2,6-dichlorobenzyloxymethyl)-4'-methyltetrahydrofuran-2'-yl)methyl]malonate

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Technology Process of diethyl (2'S,4'R,5'R)-2-[(5'-(2,6-dichlorobenzyloxymethyl)-4'-methyltetrahydrofuran-2'-yl)methyl]malonate

There total 7 articles about diethyl (2'S,4'R,5'R)-2-[(5'-(2,6-dichlorobenzyloxymethyl)-4'-methyltetrahydrofuran-2'-yl)methyl]malonate 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:

: 930795-47-4
(3R,4R)-4,5-bis(2,6-dichlorobenzyloxy)-3-methylpentanal

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

Guidance literature:: Multi-step reaction with 3 steps

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

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

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

3.1: NaH / dimethylformamide / 0.5 h

3.2: dimethylformamide / 90 °C

With n-butyllithium; iodine; sodium hydride; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; acetonitrile; 1.2: Wittig olefination;
DOI:10.1021/jo062396o

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 5 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

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

Reference yield:

: 930795-13-4
(4R,5R)-5,6-bis(2,6-dichlorobenzyloxy)-4-methylhex-1-ene

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

Guidance literature:: Multi-step reaction with 2 steps

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

2.1: NaH / dimethylformamide / 0.5 h

2.2: dimethylformamide / 90 °C

With iodine; sodium hydride; In N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo062396o