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

Base Information

Chemical Name:[(2S,4S,6S)-6-Methoxy-4-(4-methoxy-benzyloxy)-5,5-dimethyl-tetrahydro-pyran-2-yl]-methanol
CAS No.:913722-23-3
Molecular Formula:C₁₇H₂₆O₅
Molecular Weight:310.39
Hs Code.:

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

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Chemical Property of [(2S,4S,6S)-6-Methoxy-4-(4-methoxy-benzyloxy)-5,5-dimethyl-tetrahydro-pyran-2-yl]-methanol

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Technology Process of [(2S,4S,6S)-6-Methoxy-4-(4-methoxy-benzyloxy)-5,5-dimethyl-tetrahydro-pyran-2-yl]-methanol

There total 6 articles about [(2S,4S,6S)-6-Methoxy-4-(4-methoxy-benzyloxy)-5,5-dimethyl-tetrahydro-pyran-2-yl]-methanol 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: 98.0%

: 913722-22-2
tert-Butyl-[(2S,4S,6S)-6-methoxy-4-(4-methoxy-benzyloxy)-5,5-dimethyl-tetrahydro-pyran-2-ylmethoxy]-diphenyl-silane

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

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2.5h;
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

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

Guidance literature:: Multi-step reaction with 6 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

With 1H-imidazole; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; trimethylaluminum; tri-n-butyl-tin hydride; pyridinium p-toluenesulfonate; isopropyl alcohol; 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

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

Guidance literature:: Multi-step reaction with 3 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

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