(2R)-2-(benzyloxy)-3-[(2S,5S)-5-methyl-6-oxo-tetrahydro-2H-pyran-2-yl]propanal

Base Information

Chemical Name:(2R)-2-(benzyloxy)-3-[(2S,5S)-5-methyl-6-oxo-tetrahydro-2H-pyran-2-yl]propanal
CAS No.:502160-06-7
Molecular Formula:C₁₆H₂₀O₄
Molecular Weight:276.332
Hs Code.:

Synonyms:(2R)-2-(benzyloxy)-3-[(2S,5S)-5-methyl-6-oxo-tetrahydro-2H-pyran-2-yl]propanal

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Chemical Property of (2R)-2-(benzyloxy)-3-[(2S,5S)-5-methyl-6-oxo-tetrahydro-2H-pyran-2-yl]propanal

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Technology Process of (2R)-2-(benzyloxy)-3-[(2S,5S)-5-methyl-6-oxo-tetrahydro-2H-pyran-2-yl]propanal

There total 12 articles about (2R)-2-(benzyloxy)-3-[(2S,5S)-5-methyl-6-oxo-tetrahydro-2H-pyran-2-yl]propanal 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: 82.0%

: 913193-94-9
(3S,6S)-6-((2R)-2-benzyloxy-3-hydroxypropyl)-3-methyltetrahydropyran-2-one

: 502160-06-7
(2R)-2-(benzyloxy)-3-[(2S,5S)-5-methyl-6-oxo-tetrahydro-2H-pyran-2-yl]propanal

Guidance literature:: With pyridine; Dess-Martin periodane; In dichloromethane; at 20 ℃; for 0.75h;
DOI:10.1021/jo0610412

Reference yield:

: 913193-77-8
(2S,5S,7R)-7-Benzyloxy-5,8-dihydroxy-2-methyl-octanoic acid

: 502160-06-7
(2R)-2-(benzyloxy)-3-[(2S,5S)-5-methyl-6-oxo-tetrahydro-2H-pyran-2-yl]propanal

Guidance literature:: Multi-step reaction with 2 steps

1: 90 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 24 h / 20 °C

2: 82 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 0.75 h / 20 °C

With pyridine; pyridinium p-toluenesulfonate; Dess-Martin periodane; In dichloromethane; 2: Dess-Martin oxidation;
DOI:10.1021/jo0610412

Reference yield:

: 913193-72-3
(3R)-3-benzyloxy-4-(tert-butyldiphenylsilanyloxy)butyraldehyde

: 502160-06-7
(2R)-2-(benzyloxy)-3-[(2S,5S)-5-methyl-6-oxo-tetrahydro-2H-pyran-2-yl]propanal

Guidance literature:: Multi-step reaction with 10 steps

1.1: 80 percent / TiCl₄ / CH₂Cl₂ / 0.33 h / -78 °C

2.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

3.1: O₃; pyridine / methanol; CH₂Cl₂ / 0.75 h / -78 °C

3.2: 99 percent / Me₂S / methanol; CH₂Cl₂ / 12 h / -78 - 20 °C

4.1: 95 percent / NaBH₄ / methanol / 0.33 h / 0 °C

5.1: 92 percent / (PhO)3PCH₃⁽¹⁺⁾*I^(1-) / dimethylformamide / 1 h / 0 °C

6.1: 95 percent / tetrahydrofuran; hexane / 8 h / 0 °C

7.1: tetrabutylammonium fluoride / tetrahydrofuran / 6 h / 0 °C

8.1: 1.47 g / tetra-n-butylammonium hydroxide / 2-methyl-propan-2-ol; H₂O / 24 h / Heating

9.1: 90 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 24 h / 20 °C

10.1: 82 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 0.75 h / 20 °C

With pyridine; 2,6-dimethylpyridine; sodium tetrahydroborate; tetrabutyl ammonium fluoride; tetra(n-butyl)ammonium hydroxide; methyltriphenoxyphosphonium iodide; pyridinium p-toluenesulfonate; titanium tetrachloride; Dess-Martin periodane; ozone; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 10.1: Dess-Martin oxidation;
DOI:10.1021/jo0610412