benzyl (2S)-2-<(2R,3R,5S,6S)-2-hydroxy-3,5-dimethyl-6-((1S)-1-methyl-2-oxoethyl)tetrahydropyran-2-yl>propanoate

Base Information

Chemical Name:benzyl (2S)-2-<(2R,3R,5S,6S)-2-hydroxy-3,5-dimethyl-6-((1S)-1-methyl-2-oxoethyl)tetrahydropyran-2-yl>propanoate
CAS No.:110815-04-8
Molecular Formula:C₂₀H₂₈O₅
Molecular Weight:348.439
Hs Code.:

Synonyms:benzyl (2S)-2-<(2R,3R,5S,6S)-2-hydroxy-3,5-dimethyl-6-((1S)-1-methyl-2-oxoethyl)tetrahydropyran-2-yl>propanoate

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Chemical Property of benzyl (2S)-2-<(2R,3R,5S,6S)-2-hydroxy-3,5-dimethyl-6-((1S)-1-methyl-2-oxoethyl)tetrahydropyran-2-yl>propanoate

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Technology Process of benzyl (2S)-2-<(2R,3R,5S,6S)-2-hydroxy-3,5-dimethyl-6-((1S)-1-methyl-2-oxoethyl)tetrahydropyran-2-yl>propanoate

There total 14 articles about benzyl (2S)-2-<(2R,3R,5S,6S)-2-hydroxy-3,5-dimethyl-6-((1S)-1-methyl-2-oxoethyl)tetrahydropyran-2-yl>propanoate 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: 85.0%

: 110815-03-7
benzyl (2S)-2-<(2R,3R,5S,6S)-2-hydroxy-3,5-dimethyl-6-((1S)-1-methyl-2-hydroxyethyl)tetrahydropyran-2-yl>propanoate

: 110815-04-8
benzyl (2S)-2-<(2R,3R,5S,6S)-2-hydroxy-3,5-dimethyl-6-((1S)-1-methyl-2-oxoethyl)tetrahydropyran-2-yl>propanoate

Guidance literature:: With sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine; In dichloromethane; at 0 ℃; for 0.5h;
DOI:10.1021/ja00020a025

Reference yield:

: 110814-97-6
<4-(1S,3R)-2R,4S,5S>-2-(1-naphthyl)-4-(1,3-dimethyl-4-oxobutyl)-5-methyl-1,3-dioxane

: 110815-04-8
benzyl (2S)-2-<(2R,3R,5S,6S)-2-hydroxy-3,5-dimethyl-6-((1S)-1-methyl-2-oxoethyl)tetrahydropyran-2-yl>propanoate

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) di-n-butylboryl triflate, triethylamine / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) CH₂Cl₂, a) -78 deg C, 1 h, b) 0 deg C, 1 h

2: 91 percent / (N,N-dimethylamino)pyridine / CH₂Cl₂ / 5 h / Ambient temperature

3: 1.) 2.4 M n-butyllithium / 1.) THF, hexane, 0 deg C, 20 min, 2.) THF, -hexane, 20 deg C, 24 h

5: 85 percent / triethylamine, dimethyl sulfoxide, pyridine sulfur trioxide complex / CH₂Cl₂ / 0.5 h / 0 °C

With dmap; n-butyllithium; di-n-butylboryl trifluoromethanesulfonate; sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine; In dichloromethane;
DOI:10.1021/ja00020a025

Reference yield:

: 110838-51-2
benzyl (2S,3R,6S,7S,8S)-2,4,6,8-tetramethyl-3-<(trimethylsilyl)oxy>-7,9-((R)-naphthylmethylenedioxy)-1-nonanoate

: 110815-04-8
benzyl (2S)-2-<(2R,3R,5S,6S)-2-hydroxy-3,5-dimethyl-6-((1S)-1-methyl-2-oxoethyl)tetrahydropyran-2-yl>propanoate

Guidance literature:: Multi-step reaction with 2 steps

2: 85 percent / triethylamine, dimethyl sulfoxide, pyridine sulfur trioxide complex / CH₂Cl₂ / 0.5 h / 0 °C

With sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine; In dichloromethane;
DOI:10.1021/ja00020a025