(2R,3S)-2-(2-Benzyloxy-ethyl)-3-hydroxy-2-methyl-succinic acid diethyl ester

Base Information

Chemical Name:(2R,3S)-2-(2-Benzyloxy-ethyl)-3-hydroxy-2-methyl-succinic acid diethyl ester
CAS No.:202846-62-6
Molecular Formula:C₁₈H₂₆O₆
Molecular Weight:338.401
Hs Code.:

Synonyms:(2R,3S)-2-(2-Benzyloxy-ethyl)-3-hydroxy-2-methyl-succinic acid diethyl ester

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Chemical Property of (2R,3S)-2-(2-Benzyloxy-ethyl)-3-hydroxy-2-methyl-succinic acid diethyl ester

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Technology Process of (2R,3S)-2-(2-Benzyloxy-ethyl)-3-hydroxy-2-methyl-succinic acid diethyl ester

There total 1 articles about (2R,3S)-2-(2-Benzyloxy-ethyl)-3-hydroxy-2-methyl-succinic acid diethyl ester 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: 67.0%

: 54555-84-9
benzyl iodoethyl ether

: 73840-71-8
diethyl (2S,3R)-(+)-2-hydroxy-3-methylsuccinate

: 202846-62-6
(2R,3S)-2-(2-Benzyloxy-ethyl)-3-hydroxy-2-methyl-succinic acid diethyl ester

Guidance literature:: diethyl (2S,3R)-(+)-2-hydroxy-3-methylsuccinate; With lithium diisopropyl amide; In tetrahydrofuran; hexane; at -78 ℃; for 3h;

benzyl iodoethyl ether; In tetrahydrofuran; hexane; at -78 - 0 ℃; for 21h;
DOI:10.1002/jhet.5570380124

Reference yield:

: 202846-62-6
(2R,3S)-2-(2-Benzyloxy-ethyl)-3-hydroxy-2-methyl-succinic acid diethyl ester

: 344357-32-0
(S)-3-[(3R,4S)-1-Hydroxy-3-(4-methoxy-benzyloxy)-4-methyl-hexyl]-3-methoxymethoxy-4-methyl-4-vinyl-dihydro-furan-2-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: 97 percent / aq. KOH / methanol / 72 h / 20 °C

2.1: 74 percent / lithium triethylborohydride / tetrahydrofuran / 40 h / 20 °C

3.1: 93 percent / diisopropylethylamine / CH₂Cl₂ / 48 h / Heating

4.1: 96 percent / H₂ / 10 percent Pd/C / ethanol / 44 h / 20 °C

5.1: 88 percent / tri-n-butylphosphine / tetrahydrofuran / 1 h / 20 °C

6.1: 76 percent / 30 percent aq. H₂O₂ / tetrahydrofuran / 5 h / 20 °C

7.1: LDA / tetrahydrofuran; hexane / -78 °C

7.2: 84 percent / tetrahydrofuran; hexane / 3.5 h / -78 °C

With potassium hydroxide; tributylphosphine; hydrogen; dihydrogen peroxide; lithium triethylborohydride; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane;
DOI:10.1002/jhet.5570380124

Reference yield:

: 202846-62-6
(2R,3S)-2-(2-Benzyloxy-ethyl)-3-hydroxy-2-methyl-succinic acid diethyl ester

: 344357-26-2
(3R,4R,3'R,4'S)-3-[3'-(4-methoxybenzyloxy)-4'-methylhexanoyl]-3-methoxymethyloxy-4-methyl-4-vinyl-γ-butyrolactone

Guidance literature:: Multi-step reaction with 8 steps

1.1: 97 percent / aq. KOH / methanol / 72 h / 20 °C

2.1: 74 percent / lithium triethylborohydride / tetrahydrofuran / 40 h / 20 °C

3.1: 93 percent / diisopropylethylamine / CH₂Cl₂ / 48 h / Heating

4.1: 96 percent / H₂ / 10 percent Pd/C / ethanol / 44 h / 20 °C

5.1: 88 percent / tri-n-butylphosphine / tetrahydrofuran / 1 h / 20 °C

6.1: 76 percent / 30 percent aq. H₂O₂ / tetrahydrofuran / 5 h / 20 °C

7.1: LDA / tetrahydrofuran; hexane / -78 °C

7.2: 84 percent / tetrahydrofuran; hexane / 3.5 h / -78 °C

8.1: 50 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

With potassium hydroxide; tributylphosphine; hydrogen; dihydrogen peroxide; lithium triethylborohydride; Dess-Martin periodane; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane;
DOI:10.1002/jhet.5570380124