(2S,3R,4R)-5-Benzyloxymethoxy-2,4-dimethyl-pentane-1,3,4-triol

Base Information

Chemical Name:(2S,3R,4R)-5-Benzyloxymethoxy-2,4-dimethyl-pentane-1,3,4-triol
CAS No.:85091-03-8
Molecular Formula:C₁₅H₂₄O₅
Molecular Weight:284.353
Hs Code.:

Synonyms:(2S,3R,4R)-5-Benzyloxymethoxy-2,4-dimethyl-pentane-1,3,4-triol

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Chemical Property of (2S,3R,4R)-5-Benzyloxymethoxy-2,4-dimethyl-pentane-1,3,4-triol

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Technology Process of (2S,3R,4R)-5-Benzyloxymethoxy-2,4-dimethyl-pentane-1,3,4-triol

There total 7 articles about (2S,3R,4R)-5-Benzyloxymethoxy-2,4-dimethyl-pentane-1,3,4-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: 92.0%

: 85091-02-7
(3R,4R,5R)-5-Benzyloxymethoxymethyl-4-hydroxy-3,5-dimethyl-dihydro-furan-2-one

: 85091-03-8
(2S,3R,4R)-5-Benzyloxymethoxy-2,4-dimethyl-pentane-1,3,4-triol

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; for 18h; Ambient temperature;
DOI:10.1016/S0040-4039(00)88703-1

Reference yield:

: 85090-98-8
(2R,3R)-3-Hydroxy-2,4-dimethyl-pent-4-enoic acid

: 85091-03-8
(2S,3R,4R)-5-Benzyloxymethoxy-2,4-dimethyl-pentane-1,3,4-triol

Guidance literature:: Multi-step reaction with 5 steps

1: imidazole / tetrahydrofuran / 12 h / Ambient temperature

2: 80 percent / VO(OEt)3, t-BuOOH, NaOAc / CH₂Cl₂ / 18 h / 0 °C

3: 100 percent / 1percent HF / acetonitrile / 0.25 h / Ambient temperature

4: 98 percent / diisopropylethylamine / tetrahydrofuran / 24 h

5: 92 percent / LAH / tetrahydrofuran / 18 h / Ambient temperature

With 1H-imidazole; tert.-butylhydroperoxide; lithium aluminium tetrahydride; hydrogen fluoride; sodium acetate; vanadium(V) oxytriethoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1016/S0040-4039(00)88703-1

Reference yield:

: 85090-97-7
(1S,3R,4R)-1-Cyclohexyl-1,4-dihydroxy-3,5-dimethyl-hex-5-en-2-one

: 85091-03-8
(2S,3R,4R)-5-Benzyloxymethoxy-2,4-dimethyl-pentane-1,3,4-triol

Guidance literature:: Multi-step reaction with 6 steps

1: NaIO₄ / methanol; H₂O / 2 h / Ambient temperature

2: imidazole / tetrahydrofuran / 12 h / Ambient temperature

3: 80 percent / VO(OEt)3, t-BuOOH, NaOAc / CH₂Cl₂ / 18 h / 0 °C

4: 100 percent / 1percent HF / acetonitrile / 0.25 h / Ambient temperature

5: 98 percent / diisopropylethylamine / tetrahydrofuran / 24 h

6: 92 percent / LAH / tetrahydrofuran / 18 h / Ambient temperature

With 1H-imidazole; tert.-butylhydroperoxide; sodium periodate; lithium aluminium tetrahydride; hydrogen fluoride; sodium acetate; vanadium(V) oxytriethoxide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile;
DOI:10.1016/S0040-4039(00)88703-1