((2S,3R,5R)-5-Benzyloxymethyl-3-methyl-tetrahydro-furan-2-yl)-acetic acid ethyl ester

Base Information

Chemical Name:((2S,3R,5R)-5-Benzyloxymethyl-3-methyl-tetrahydro-furan-2-yl)-acetic acid ethyl ester
CAS No.:343950-02-7
Molecular Formula:C₁₇H₂₄O₄
Molecular Weight:292.375
Hs Code.:

Synonyms:((2S,3R,5R)-5-Benzyloxymethyl-3-methyl-tetrahydro-furan-2-yl)-acetic acid ethyl ester

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Chemical Property of ((2S,3R,5R)-5-Benzyloxymethyl-3-methyl-tetrahydro-furan-2-yl)-acetic acid ethyl ester

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Technology Process of ((2S,3R,5R)-5-Benzyloxymethyl-3-methyl-tetrahydro-furan-2-yl)-acetic acid ethyl ester

There total 2 articles about ((2S,3R,5R)-5-Benzyloxymethyl-3-methyl-tetrahydro-furan-2-yl)-acetic acid ethyl 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: 94.0%

: ethyl (4R,6R)-7-benzyloxy-6-hydroxy-4-mathyl-2-heptenoate

: 343950-02-7
((2S,3R,5R)-5-Benzyloxymethyl-3-methyl-tetrahydro-furan-2-yl)-acetic acid ethyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 0.5h;
DOI:10.1021/ol015741z

Reference yield:

: (4R,6R)-6-hydroxymethyl-4-methyl-γ-butyrolactone

: 343950-02-7
((2S,3R,5R)-5-Benzyloxymethyl-3-methyl-tetrahydro-furan-2-yl)-acetic acid ethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: DIBAL / CH₂Cl₂; hexane / 0.5 h / -78 °C

1.2: aq. potassium sodium tartrate / CH₂Cl₂; hexane; methanol / 1 h / 20 °C

1.3: 6.30 g / benzene / 20 h / 80 °C

2.1: 94 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C

With tetrabutyl ammonium fluoride; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane; 1.3: Wittig olefination / 2.1: Michael reaction;
DOI:10.1021/ol015741z

Reference yield: 91.0%

: 343950-02-7
((2S,3R,5R)-5-Benzyloxymethyl-3-methyl-tetrahydro-furan-2-yl)-acetic acid ethyl ester

: 343949-98-4
(2'S,3'R,5'R)-2-(5'benzyloxymethyl-3'-methyl-tetrahydrofuran-2'-yl)-ethanol

Guidance literature:: ((2S,3R,5R)-5-Benzyloxymethyl-3-methyl-tetrahydro-furan-2-yl)-acetic acid ethyl ester; With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 ℃; for 1.5h;

With Rochelle's salt; In methanol; hexane; dichloromethane; at 20 ℃; for 1h; Further stages.;
DOI:10.1021/ol015741z