(-)-(2S,4S)-1-(benzyloxy)-6,6-dimethoxyhexane-2,4-diol

Base Information

Chemical Name:(-)-(2S,4S)-1-(benzyloxy)-6,6-dimethoxyhexane-2,4-diol
CAS No.:941295-52-9
Molecular Formula:C₁₅H₂₄O₅
Molecular Weight:284.353
Hs Code.:

Synonyms:(-)-(2S,4S)-1-(benzyloxy)-6,6-dimethoxyhexane-2,4-diol

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Chemical Property of (-)-(2S,4S)-1-(benzyloxy)-6,6-dimethoxyhexane-2,4-diol

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Technology Process of (-)-(2S,4S)-1-(benzyloxy)-6,6-dimethoxyhexane-2,4-diol

There total 10 articles about (-)-(2S,4S)-1-(benzyloxy)-6,6-dimethoxyhexane-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: 95.0%

: 941295-57-4
(-)-(R)-1-(benzyloxy)-4-hydroxy-6,6-dimethoxyhexan-2-one

: 941295-52-9
(-)-(2S,4S)-1-(benzyloxy)-6,6-dimethoxyhexane-2,4-diol

Guidance literature:: With sodium tris(acetoxy)borohydride; acetic acid; In acetonitrile; at -20 ℃; for 1h;
DOI:10.1021/ol070405p

Reference yield:

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

: 941295-52-9
(-)-(2S,4S)-1-(benzyloxy)-6,6-dimethoxyhexane-2,4-diol

Guidance literature:: Multi-step reaction with 6 steps

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

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

3: D-diethyl tartrate; tert-butyl hydroperoxide / Ti(Oi-Pr)4 / CH₂Cl₂; decane / 48 h / -20 °C

4: 88 percent / Dess-Martin periodinane / CH₂Cl₂ / 8.5 h / 0 - 20 °C

5: 86 percent / SmI₂ / tetrahydrofuran / 1.33 h / -90 - -78 °C

6: 95 percent / NaBH(OAc)3; AcOH / acetonitrile / 1 h / -20 °C

With tert.-butylhydroperoxide; samarium diiodide; S-alpine borane; Diethyl tartrate; isobutylmagnesium bromide; sodium tris(acetoxy)borohydride; Dess-Martin periodane; acetic acid; titanium(IV) isopropylate; bis(cyclopentadienyl)titanium dichloride; In tetrahydrofuran; diethyl ether; decane; dichloromethane; acetonitrile; 3: Sharpless epoxidation;
DOI:10.1021/ol070405p

Reference yield:

: 941295-60-9
(+)-(S)-1-(benzyloxy)-6,6-dimethoxyhex-3-yn-2-ol

: 941295-52-9
(-)-(2S,4S)-1-(benzyloxy)-6,6-dimethoxyhexane-2,4-diol

Guidance literature:: Multi-step reaction with 5 steps

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

2: D-diethyl tartrate; tert-butyl hydroperoxide / Ti(Oi-Pr)4 / CH₂Cl₂; decane / 48 h / -20 °C

3: 88 percent / Dess-Martin periodinane / CH₂Cl₂ / 8.5 h / 0 - 20 °C

4: 86 percent / SmI₂ / tetrahydrofuran / 1.33 h / -90 - -78 °C

5: 95 percent / NaBH(OAc)3; AcOH / acetonitrile / 1 h / -20 °C

With tert.-butylhydroperoxide; samarium diiodide; Diethyl tartrate; isobutylmagnesium bromide; sodium tris(acetoxy)borohydride; Dess-Martin periodane; acetic acid; titanium(IV) isopropylate; bis(cyclopentadienyl)titanium dichloride; In tetrahydrofuran; diethyl ether; decane; dichloromethane; acetonitrile; 2: Sharpless epoxidation;
DOI:10.1021/ol070405p