(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-(prop-1-en-2-yl)benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Base Information

Chemical Name:(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-(prop-1-en-2-yl)benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
CAS No.:1118566-91-8
Molecular Formula:C₃₀H₃₃ClO₉
Molecular Weight:573.04
Hs Code.:

Synonyms:(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-(prop-1-en-2-yl)benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

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Chemical Property of (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-(prop-1-en-2-yl)benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

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Technology Process of (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-(prop-1-en-2-yl)benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

There total 11 articles about (2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-(prop-1-en-2-yl)benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate 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: 76.0%

: 1118566-90-7
(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(3-(4-acetylbenzyl)-4-chlorophenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

: 2065-66-9
methyl-triphenylphosphonium iodide

: 1118566-91-8
(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-(prop-1-en-2-yl)benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Guidance literature:: With potassium hexamethylsilazane; In toluene; at 20 ℃;
DOI:10.1016/j.bmcl.2011.06.032

Reference yield:

: 1185339-44-9
C₁₉H₂₁ClO₅

: 1118566-91-8
(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-(prop-1-en-2-yl)benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Guidance literature:: Multi-step reaction with 3 steps

1: dmap / pyridine; dichloromethane / 20 °C

2: aluminum (III) chloride / dichloromethane / 0 - 20 °C

3: potassium hexamethylsilazane / toluene / 20 °C

With dmap; aluminum (III) chloride; potassium hexamethylsilazane; In pyridine; dichloromethane; toluene; 2: Friedel Crafts acylation / 3: Wittig reaction;
DOI:10.1016/j.bmcl.2011.06.032

Reference yield:

: 312749-31-8
2-chloro-5-bromobenzophenone

: 1118566-91-8
(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-(prop-1-en-2-yl)benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Guidance literature:: Multi-step reaction with 7 steps

1: triethylsilane; trifluorormethanesulfonic acid; trifluoroacetic acid / Reflux

2: n-butyllithium / tetrahydrofuran; toluene / -78 °C

3: methanesulfonic acid / methanesulfonic acid / -78 - 20 °C

4: triethylsilane; boron trifluoride diethyl etherate / dichloromethane; acetonitrile / -30 - -10 °C

5: dmap / pyridine; dichloromethane / 20 °C

6: aluminum (III) chloride / dichloromethane / 0 - 20 °C

7: potassium hexamethylsilazane / toluene / 20 °C

With triethylsilane; dmap; aluminum (III) chloride; n-butyllithium; methanesulfonic acid; trifluorormethanesulfonic acid; boron trifluoride diethyl etherate; potassium hexamethylsilazane; trifluoroacetic acid; In tetrahydrofuran; pyridine; methanesulfonic acid; dichloromethane; toluene; acetonitrile; 6: Friedel Crafts acylation / 7: Wittig reaction;
DOI:10.1016/j.bmcl.2011.06.032