(2S,4S,6S)-6-Methoxy-4-(4-methoxy-benzyloxy)-5,5-dimethyl-tetrahydro-pyran-2-carbaldehyde

Base Information

Chemical Name:(2S,4S,6S)-6-Methoxy-4-(4-methoxy-benzyloxy)-5,5-dimethyl-tetrahydro-pyran-2-carbaldehyde
CAS No.:913722-24-4
Molecular Formula:C₁₇H₂₄O₅
Molecular Weight:308.375
Hs Code.:

Synonyms:(2S,4S,6S)-6-Methoxy-4-(4-methoxy-benzyloxy)-5,5-dimethyl-tetrahydro-pyran-2-carbaldehyde

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Chemical Property of (2S,4S,6S)-6-Methoxy-4-(4-methoxy-benzyloxy)-5,5-dimethyl-tetrahydro-pyran-2-carbaldehyde

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Technology Process of (2S,4S,6S)-6-Methoxy-4-(4-methoxy-benzyloxy)-5,5-dimethyl-tetrahydro-pyran-2-carbaldehyde

There total 8 articles about (2S,4S,6S)-6-Methoxy-4-(4-methoxy-benzyloxy)-5,5-dimethyl-tetrahydro-pyran-2-carbaldehyde 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:

: 913722-23-3
[(2S,4S,6S)-6-Methoxy-4-(4-methoxy-benzyloxy)-5,5-dimethyl-tetrahydro-pyran-2-yl]-methanol

: 913722-24-4
(2S,4S,6S)-6-Methoxy-4-(4-methoxy-benzyloxy)-5,5-dimethyl-tetrahydro-pyran-2-carbaldehyde

Guidance literature:: With 4-methylmorpholine N-oxide; tetrapropylammonium perruthennate; In dichloromethane; at 20 ℃; for 0.5h;
DOI:10.1021/ol061626i

Reference yield:

: 913722-16-4
(2S,5R,6R)-5-Hydroxy-6-hydroxymethyl-2-methoxy-3,3-dimethyl-tetrahydro-pyran-4-one

: 913722-24-4
(2S,4S,6S)-6-Methoxy-4-(4-methoxy-benzyloxy)-5,5-dimethyl-tetrahydro-pyran-2-carbaldehyde

Guidance literature:: Multi-step reaction with 7 steps

1: 91 percent / imidazole / dimethylformamide / 2 h / 20 °C

2: 83 percent / acetonitrile / 22 h / 20 °C

3: 95 percent / Bu₃SnH; AIBN / toluene / 0.83 h / 90 °C

4: 84 percent / Me₃Al; i-PrOH / hexane / 24 h / 20 °C

5: 77 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 48 h / 20 °C

6: 98 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 2.5 h / 20 °C

7: N-methylmorpholine N-oxide / tetra-n-propylammonium perruthenate / CH₂Cl₂ / 0.5 h / 20 °C

With 1H-imidazole; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; trimethylaluminum; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; 4-methylmorpholine N-oxide; isopropyl alcohol; tetrapropylammonium perruthennate; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 3: Barton deoxygenation / 4: Meerwein-Ponndorf-Verley reduction;
DOI:10.1021/ol061626i

Reference yield:

: 913722-19-7
(2S,6S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-2-methoxy-3,3-dimethyl-tetrahydro-pyran-4-one

: 913722-24-4
(2S,4S,6S)-6-Methoxy-4-(4-methoxy-benzyloxy)-5,5-dimethyl-tetrahydro-pyran-2-carbaldehyde

Guidance literature:: Multi-step reaction with 4 steps

1: 84 percent / Me₃Al; i-PrOH / hexane / 24 h / 20 °C

2: 77 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 48 h / 20 °C

3: 98 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 2.5 h / 20 °C

4: N-methylmorpholine N-oxide / tetra-n-propylammonium perruthenate / CH₂Cl₂ / 0.5 h / 20 °C

With tetrabutyl ammonium fluoride; trimethylaluminum; pyridinium p-toluenesulfonate; 4-methylmorpholine N-oxide; isopropyl alcohol; tetrapropylammonium perruthennate; In tetrahydrofuran; hexane; dichloromethane; 1: Meerwein-Ponndorf-Verley reduction;
DOI:10.1021/ol061626i