((2S,3S,4S,5S)-4-Benzyloxy-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl)-acetaldehyde

Base Information

Chemical Name:((2S,3S,4S,5S)-4-Benzyloxy-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl)-acetaldehyde
CAS No.:359868-27-2
Molecular Formula:C₁₆H₂₀O₄
Molecular Weight:276.332
Hs Code.:

Synonyms:((2S,3S,4S,5S)-4-Benzyloxy-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl)-acetaldehyde

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Chemical Property of ((2S,3S,4S,5S)-4-Benzyloxy-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl)-acetaldehyde

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Technology Process of ((2S,3S,4S,5S)-4-Benzyloxy-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl)-acetaldehyde

There total 9 articles about ((2S,3S,4S,5S)-4-Benzyloxy-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl)-acetaldehyde 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: 71.0%

: 359868-26-1
(3R,4R,5S,6S)-5-Benzyloxy-4,6-dimethyl-heptane-1,3,7-triol

: 359868-27-2
((2S,3S,4S,5S)-4-Benzyloxy-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl)-acetaldehyde

Guidance literature:: With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In dichloromethane; dimethyl sulfoxide; at 20 ℃; for 6h;
DOI:10.1016/S0040-4039(01)00799-7

Reference yield:

: 96691-92-8
(1R,2R,3r,4S,5S)-3-(benzyloxy)-2,4-dimethyl-8-oxa-bicyclo[3.2.1]oct-6-ene

: 359868-27-2
((2S,3S,4S,5S)-4-Benzyloxy-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl)-acetaldehyde

Guidance literature:: Multi-step reaction with 9 steps

1.1: (+)-diisopinocampheylborane / 24 h / -23 °C

1.2: 96 percent / NaOH; H₂O₂ / H₂O / 6 h / 20 °C

2.1: PCC / CH₂Cl₂ / 3 h / 20 °C

3.1: m-CPBA; NaHCO₃ / CH₂Cl₂ / 10 h / 20 °C

4.1: 88 percent / LiAlH₄ / tetrahydrofuran / 4 h / 0 - 20 °C

5.1: 83 percent / imidazole / CH₂Cl₂ / 2 h / 0 - 20 °C

6.1: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

7.1: NaBH₄ / methanol; tetrahydrofuran / 1 h / 0 - 20 °C

8.1: 88 percent / TBAF / tetrahydrofuran / 1.5 h / 20 °C

9.1: 71 percent / IBX / dimethylsulfoxide; CH₂Cl₂ / 6 h / 20 °C

With 1H-imidazole; sodium tetrahydroborate; lithium aluminium tetrahydride; diisopinocampheylborane; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; Dess-Martin periodane; 3-chloro-benzenecarboperoxoic acid; pyridinium chlorochromate; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; 3.1: Baeyer-Villiger oxidation;
DOI:10.1016/S0040-4039(01)00799-7

Reference yield:

: 171231-75-7
endo-3-benzyloxy-endo,endo-2,4-dimethyl-6,9-dioxabicyclo[3.2.1]non-7-one

: 359868-27-2
((2S,3S,4S,5S)-4-Benzyloxy-3,5-dimethyl-6-oxo-tetrahydro-pyran-2-yl)-acetaldehyde

Guidance literature:: Multi-step reaction with 6 steps

1: 88 percent / LiAlH₄ / tetrahydrofuran / 4 h / 0 - 20 °C

2: 83 percent / imidazole / CH₂Cl₂ / 2 h / 0 - 20 °C

3: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

4: NaBH₄ / methanol; tetrahydrofuran / 1 h / 0 - 20 °C

5: 88 percent / TBAF / tetrahydrofuran / 1.5 h / 20 °C

6: 71 percent / IBX / dimethylsulfoxide; CH₂Cl₂ / 6 h / 20 °C

With 1H-imidazole; sodium tetrahydroborate; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; Dess-Martin periodane; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide;
DOI:10.1016/S0040-4039(01)00799-7