(-)-(2R,3S,4R)-1-(benzyloxy)-6,6-dimethoxy-3-methylhexane-2,4-diol

Base Information

Chemical Name:(-)-(2R,3S,4R)-1-(benzyloxy)-6,6-dimethoxy-3-methylhexane-2,4-diol
CAS No.:941295-93-8
Molecular Formula:C₁₆H₂₆O₅
Molecular Weight:298.379
Hs Code.:

Synonyms:(-)-(2R,3S,4R)-1-(benzyloxy)-6,6-dimethoxy-3-methylhexane-2,4-diol

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Chemical Property of (-)-(2R,3S,4R)-1-(benzyloxy)-6,6-dimethoxy-3-methylhexane-2,4-diol

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Technology Process of (-)-(2R,3S,4R)-1-(benzyloxy)-6,6-dimethoxy-3-methylhexane-2,4-diol

There total 11 articles about (-)-(2R,3S,4R)-1-(benzyloxy)-6,6-dimethoxy-3-methylhexane-2,4-diol 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:

: 941295-58-5
1-(benzyloxy)-6,6-dimethoxyhex-3-yn-2-one

: 941295-93-8
(-)-(2R,3S,4R)-1-(benzyloxy)-6,6-dimethoxy-3-methylhexane-2,4-diol

Guidance literature:: Multi-step reaction with 5 steps

1.1: (S)-Alpine Borane / tetrahydrofuran / 96 h / 20 °C

2.1: i-BuMgBr / Cp₂TiCl₂ / diethyl ether / 0 - 20 °C

3.1: NaHCO₃; m-CPBA / CH₂Cl₂ / 24 h / 20 °C

4.1: Ph₃P; p-nitrobenzoic acid; DIAD / toluene / 1.08 h / -78 - 20 °C

4.2: K₂CO₃ / methanol / 0.5 h / 20 °C

5.1: CuI / tetrahydrofuran; diethyl ether / 4.5 h / -40 - 20 °C

With copper(l) iodide; S-alpine borane; di-isopropyl azodicarboxylate; isobutylmagnesium bromide; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 4-nitro-benzoic acid; bis(cyclopentadienyl)titanium dichloride; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; 4.1: Mitsunobu inversion;
DOI:10.1021/ol070405p

Reference yield:

: 19810-31-2
Benzyloxyacetyl chloride

: 941295-93-8
(-)-(2R,3S,4R)-1-(benzyloxy)-6,6-dimethoxy-3-methylhexane-2,4-diol

Guidance literature:: Multi-step reaction with 7 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

1.2: CeCl₃ / tetrahydrofuran; hexane / 2.5 h / -78 °C

1.3: 85 percent / tetrahydrofuran; hexane / 2 h / -78 - -40 °C

2.1: (S)-Alpine Borane / tetrahydrofuran / 96 h / 20 °C

3.1: i-BuMgBr / Cp₂TiCl₂ / diethyl ether / 0 - 20 °C

4.1: NaHCO₃; m-CPBA / CH₂Cl₂ / 24 h / 20 °C

5.1: Ph₃P; p-nitrobenzoic acid; DIAD / toluene / 1.08 h / -78 - 20 °C

5.2: K₂CO₃ / methanol / 0.5 h / 20 °C

6.1: CuI / tetrahydrofuran; diethyl ether / 4.5 h / -40 - 20 °C

With copper(l) iodide; n-butyllithium; (S)-alpine borane; di-isopropyl azodicarboxylate; isobutylmagnesium bromide; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 4-nitro-benzoic acid; bis(cyclopentadienyl)titanium dichloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; 6.1: Mitsunobu inversion;
DOI:10.1021/ol070405p

Reference yield:

: 104863-68-5
2-(benzyloxy)-N-methoxy-N-methylacetamide

: 941295-93-8
(-)-(2R,3S,4R)-1-(benzyloxy)-6,6-dimethoxy-3-methylhexane-2,4-diol

Guidance literature:: Multi-step reaction with 6 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

1.2: CeCl₃ / tetrahydrofuran; hexane / 2.5 h / -78 °C

1.3: 85 percent / tetrahydrofuran; hexane / 2 h / -78 - -40 °C

2.1: (S)-Alpine Borane / tetrahydrofuran / 96 h / 20 °C

3.1: i-BuMgBr / Cp₂TiCl₂ / diethyl ether / 0 - 20 °C

4.1: NaHCO₃; m-CPBA / CH₂Cl₂ / 24 h / 20 °C

5.1: Ph₃P; p-nitrobenzoic acid; DIAD / toluene / 1.08 h / -78 - 20 °C

5.2: K₂CO₃ / methanol / 0.5 h / 20 °C

6.1: CuI / tetrahydrofuran; diethyl ether / 4.5 h / -40 - 20 °C

With copper(l) iodide; n-butyllithium; (S)-alpine borane; di-isopropyl azodicarboxylate; isobutylmagnesium bromide; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 4-nitro-benzoic acid; bis(cyclopentadienyl)titanium dichloride; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; toluene; 5.1: Mitsunobu inversion;
DOI:10.1021/ol070405p