(2S,4S,5S,6R)-6-(benzoyloxymethyl)-3,3-dimethyl-5-hydroxy-4-methoxy-2-(phenylselenyl)methyl-2H-tetrahydropyran

Base Information

Chemical Name:(2S,4S,5S,6R)-6-(benzoyloxymethyl)-3,3-dimethyl-5-hydroxy-4-methoxy-2-(phenylselenyl)methyl-2H-tetrahydropyran
CAS No.:925222-24-8
Molecular Formula:C₂₃H₂₈O₅Se
Molecular Weight:463.432
Hs Code.:

Synonyms:(2S,4S,5S,6R)-6-(benzoyloxymethyl)-3,3-dimethyl-5-hydroxy-4-methoxy-2-(phenylselenyl)methyl-2H-tetrahydropyran

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Chemical Property of (2S,4S,5S,6R)-6-(benzoyloxymethyl)-3,3-dimethyl-5-hydroxy-4-methoxy-2-(phenylselenyl)methyl-2H-tetrahydropyran

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Technology Process of (2S,4S,5S,6R)-6-(benzoyloxymethyl)-3,3-dimethyl-5-hydroxy-4-methoxy-2-(phenylselenyl)methyl-2H-tetrahydropyran

There total 1 articles about (2S,4S,5S,6R)-6-(benzoyloxymethyl)-3,3-dimethyl-5-hydroxy-4-methoxy-2-(phenylselenyl)methyl-2H-tetrahydropyran 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: 86.0%

: 925222-08-8
(2S,4S,5S,6R)-5-benzoyloxy-3,3-dimethyl-6-{[(1,1-dimethylethyl)diphenylsilyl]oxy}methyl-4-methoxy-2-(phenylselenyl)methyl-2H-tetrahydropyran

: 925222-24-8
(2S,4S,5S,6R)-6-(benzoyloxymethyl)-3,3-dimethyl-5-hydroxy-4-methoxy-2-(phenylselenyl)methyl-2H-tetrahydropyran

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 8h;
DOI:10.1021/jo0615145

Reference yield: 98.0%

: 925222-24-8
(2S,4S,5S,6R)-6-(benzoyloxymethyl)-3,3-dimethyl-5-hydroxy-4-methoxy-2-(phenylselenyl)methyl-2H-tetrahydropyran

: 109-87-5
Dimethoxymethane

: 925222-25-9
(2S,4S,5S,6R)-6-(benzoyloxymethyl)-3,3-dimethyl-4-methoxy-5-methoxymethoxy-2-(phenylselenyl)methyl-2H-tetrahydropyran

Guidance literature:: With phosphorus pentoxide; In dichloromethane; for 3h;
DOI:10.1021/jo0615145

Reference yield:

: 925222-24-8
(2S,4S,5S,6R)-6-(benzoyloxymethyl)-3,3-dimethyl-5-hydroxy-4-methoxy-2-(phenylselenyl)methyl-2H-tetrahydropyran

: 925222-27-1
(2S,4S,5S,6S)-3,3-dimethyl-4-methoxy-5-methoxymethoxy-2-(phenylselenyl)methyl-2H-tetrahydropyran-6-carboxaldehyde

Guidance literature:: Multi-step reaction with 3 steps

1: 98 percent / P₂O₅ / CH₂Cl₂ / 3 h

2: 98 percent / NaOH / methanol / 24 h / 20 °C

3: 73 percent / oxalyl chloride; triethylamine; DMSO / CH₂Cl₂ / -78 - 20 °C

With sodium hydroxide; oxalyl dichloride; phosphorus pentoxide; dimethyl sulfoxide; triethylamine; In methanol; dichloromethane; 3: Swern oxidation;
DOI:10.1021/jo0615145