3-[3-(4-methoxy-benzyloxymethyl)-but-3-enyl]-2-methyl-butane-1,2,4-triol

Base Information

Chemical Name:3-[3-(4-methoxy-benzyloxymethyl)-but-3-enyl]-2-methyl-butane-1,2,4-triol
CAS No.:915708-05-3
Molecular Formula:C₁₈H₂₈O₅
Molecular Weight:324.417
Hs Code.:

Synonyms:3-[3-(4-methoxy-benzyloxymethyl)-but-3-enyl]-2-methyl-butane-1,2,4-triol

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Chemical Property of 3-[3-(4-methoxy-benzyloxymethyl)-but-3-enyl]-2-methyl-butane-1,2,4-triol

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Technology Process of 3-[3-(4-methoxy-benzyloxymethyl)-but-3-enyl]-2-methyl-butane-1,2,4-triol

There total 9 articles about 3-[3-(4-methoxy-benzyloxymethyl)-but-3-enyl]-2-methyl-butane-1,2,4-triol 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:

: 2-(tert-butyl-dimethyl-silanyloxy)-3-[3-(4-methoxy-benzyloxymethyl)-but-3-enyl]-2-methyl-butane-1,4-diol

: 915708-05-3
3-[3-(4-methoxy-benzyloxymethyl)-but-3-enyl]-2-methyl-butane-1,2,4-triol

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2h;
DOI:10.1002/anie.200602056

Reference yield:

: 915708-00-8
5-(4-methoxy-benzyloxymethyl)-hex-5-enoic acid

: 915708-05-3
3-[3-(4-methoxy-benzyloxymethyl)-but-3-enyl]-2-methyl-butane-1,2,4-triol

Guidance literature:: Multi-step reaction with 6 steps

1: 97 percent / DCC; DMAP / CH₂Cl₂ / 3.08 h / 0 - 20 °C

2: diisopropylamine; n-BuLi / tetrahydrofuran; hexane / 2 h / -78 - 20 °C

3: [Cu{(S,S)-t-Bu-box)}](OTf)2; 4 Angstroem molecular sieves / CH₂Cl₂ / 15 h / -78 °C

4: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 20 °C

5: LiAlH₄ / tetrahydrofuran / 3 h / 0 °C

6: TBAF / tetrahydrofuran / 2 h / 20 °C

With 2,6-dimethylpyridine; dmap; lithium aluminium tetrahydride; n-butyllithium; [Cu(2,2-bis(4(S)-t-Bu-oxazolidin-2-yl)propane)](OTf)2; 4 A molecular sieve; tetrabutyl ammonium fluoride; diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; hexane; dichloromethane; 3: Evans aldol reaction;
DOI:10.1002/anie.200602056

Reference yield:

: 915707-99-2
5-(4-methoxy-benzyloxymethyl)-hex-5-enoic acid methyl ester

: 915708-05-3
3-[3-(4-methoxy-benzyloxymethyl)-but-3-enyl]-2-methyl-butane-1,2,4-triol

Guidance literature:: Multi-step reaction with 7 steps

1: 96 percent / aq. NaOH / methanol / 4 h / 20 °C

2: 97 percent / DCC; DMAP / CH₂Cl₂ / 3.08 h / 0 - 20 °C

3: diisopropylamine; n-BuLi / tetrahydrofuran; hexane / 2 h / -78 - 20 °C

4: [Cu{(S,S)-t-Bu-box)}](OTf)2; 4 Angstroem molecular sieves / CH₂Cl₂ / 15 h / -78 °C

5: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 20 °C

6: LiAlH₄ / tetrahydrofuran / 3 h / 0 °C

7: TBAF / tetrahydrofuran / 2 h / 20 °C

With 2,6-dimethylpyridine; dmap; sodium hydroxide; lithium aluminium tetrahydride; n-butyllithium; [Cu(2,2-bis(4(S)-t-Bu-oxazolidin-2-yl)propane)](OTf)2; 4 A molecular sieve; tetrabutyl ammonium fluoride; diisopropylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; hexane; dichloromethane; 4: Evans aldol reaction;
DOI:10.1002/anie.200602056