(3R,4S,5R,6R)-3,5-bis(benzyloxy)-4-hydroxy-6-methyltetrahydropyran-2-one

Base Information

Chemical Name:(3R,4S,5R,6R)-3,5-bis(benzyloxy)-4-hydroxy-6-methyltetrahydropyran-2-one
CAS No.:846542-09-4
Molecular Formula:C₂₀H₂₂O₅
Molecular Weight:342.392
Hs Code.:

Synonyms:(3R,4S,5R,6R)-3,5-bis(benzyloxy)-4-hydroxy-6-methyltetrahydropyran-2-one

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Chemical Property of (3R,4S,5R,6R)-3,5-bis(benzyloxy)-4-hydroxy-6-methyltetrahydropyran-2-one

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Technology Process of (3R,4S,5R,6R)-3,5-bis(benzyloxy)-4-hydroxy-6-methyltetrahydropyran-2-one

There total 6 articles about (3R,4S,5R,6R)-3,5-bis(benzyloxy)-4-hydroxy-6-methyltetrahydropyran-2-one 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: 73.0%

: 846542-08-3
(2'R,3'S,4R,4'R,5'R)-4-benzyl-3-[2',4'-bis(benzyloxy)-5'-(tert-butyldimethylsilanyloxy)-3'-hydroxyhexanoyl]-5,5-dimethyloxazolidin-2-one

: 846542-09-4
(3R,4S,5R,6R)-3,5-bis(benzyloxy)-4-hydroxy-6-methyltetrahydropyran-2-one

Guidance literature:: With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; at 20 ℃; for 16h;
DOI:10.1039/b415943h

Reference yield:

: 846542-06-1
(2S,3R)-2-benzyloxy-3-(tert-butyldimethylsilanyloxy)butyraldehyde

: 846542-09-4
(3R,4S,5R,6R)-3,5-bis(benzyloxy)-4-hydroxy-6-methyltetrahydropyran-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: 53 percent / Et₂BOTf; i-Pr₂NEt / CH₂Cl₂; hexane / -78 - 0 °C

2: 73 percent / TBAF; AcOH / tetrahydrofuran / 16 h / 20 °C

With tetrabutyl ammonium fluoride; acetic acid; N-ethyl-N,N-diisopropylamine; diethylboron trifluoromethanesulfonate; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1039/b415943h

Reference yield:

: 846542-02-7
(2'S,3'R,4S)-4-benzyl-3-(2'-benzyloxy-3'-hydroxybutyryl)-5,5-dimethyloxazolidin-2-one

: 846542-09-4
(3R,4S,5R,6R)-3,5-bis(benzyloxy)-4-hydroxy-6-methyltetrahydropyran-2-one

Guidance literature:: Multi-step reaction with 5 steps

1: 85 percent / imidazole; DMAP / dimethylformamide / 18 h / 20 °C

2: 96 percent / DIBAL / CH₂Cl₂ / 0.33 h / -78 °C

3: 70 percent / aq. K₂CO₃ / methanol / 0.25 h / 20 °C

4: 53 percent / Et₂BOTf; i-Pr₂NEt / CH₂Cl₂; hexane / -78 - 0 °C

5: 73 percent / TBAF; AcOH / tetrahydrofuran / 16 h / 20 °C

With 1H-imidazole; dmap; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; diethylboron trifluoromethanesulfonate; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1039/b415943h