(4S,5R)-2-acetoxy-5-benzyloxy-4-methyltetrahydropyran

Base Information

Chemical Name:(4S,5R)-2-acetoxy-5-benzyloxy-4-methyltetrahydropyran
CAS No.:645413-34-9
Molecular Formula:C₁₅H₂₀O₄
Molecular Weight:264.321
Hs Code.:

Synonyms:(4S,5R)-2-acetoxy-5-benzyloxy-4-methyltetrahydropyran

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Chemical Property of (4S,5R)-2-acetoxy-5-benzyloxy-4-methyltetrahydropyran

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Technology Process of (4S,5R)-2-acetoxy-5-benzyloxy-4-methyltetrahydropyran

There total 5 articles about (4S,5R)-2-acetoxy-5-benzyloxy-4-methyltetrahydropyran 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:

: 328381-75-5
(2R,3S)-1-(tert-butyldiphenylsilyloxy)-3-methylpent-4-en-2-ol

: 645413-34-9
(4S,5R)-2-acetoxy-5-benzyloxy-4-methyltetrahydropyran

Guidance literature:: Multi-step reaction with 5 steps

1.1: TMSOTf / CH₂Cl₂; hexane / 48 h / 22 °C

2.1: BH₃*THF / tetrahydrofuran / 15 h

2.2: NaOH; aq. H₂O₂ / tetrahydrofuran / 5 h

3.1: Dess-Martin periodinane / CH₂Cl₂ / 14 h

4.1: tetrabutylammonium fluoride / tetrahydrofuran

5.1: 0.224 g / pyridine; 4-dimethylaminopyridine / 48 h

With pyridine; dmap; borane-THF; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; Dess-Martin periodane; In tetrahydrofuran; hexane; dichloromethane; 3.1: Dess-Martin oxidation;
DOI:10.1021/ja037935a

Reference yield:

: 645413-30-5
(2R,3S)-(2-benzyloxy-3-methylpent-4-enyloxy)-tert-butyldiphenylsilane

: 645413-34-9
(4S,5R)-2-acetoxy-5-benzyloxy-4-methyltetrahydropyran

Guidance literature:: Multi-step reaction with 4 steps

1.1: BH₃*THF / tetrahydrofuran / 15 h

1.2: NaOH; aq. H₂O₂ / tetrahydrofuran / 5 h

2.1: Dess-Martin periodinane / CH₂Cl₂ / 14 h

3.1: tetrabutylammonium fluoride / tetrahydrofuran

4.1: 0.224 g / pyridine; 4-dimethylaminopyridine / 48 h

With pyridine; dmap; borane-THF; tetrabutyl ammonium fluoride; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; 2.1: Dess-Martin oxidation;
DOI:10.1021/ja037935a

Reference yield:

: 645413-32-7
(3R,4S)-4-benzyloxy-5-(tert-butyldiphenylsilyloxy)-3-methylpentanal

: 645413-34-9
(4S,5R)-2-acetoxy-5-benzyloxy-4-methyltetrahydropyran

Guidance literature:: Multi-step reaction with 2 steps

1: tetrabutylammonium fluoride / tetrahydrofuran

2: 0.224 g / pyridine; 4-dimethylaminopyridine / 48 h

With pyridine; dmap; tetrabutyl ammonium fluoride; In tetrahydrofuran;
DOI:10.1021/ja037935a