(1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(4-chloro-3-(phenoxymethyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate

Base Information

Chemical Name:(1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(4-chloro-3-(phenoxymethyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate
CAS No.:1416165-44-0
Molecular Formula:C₂₈H₂₉ClO₁₁
Molecular Weight:576.985
Hs Code.:

Synonyms:(1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(4-chloro-3-(phenoxymethyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate

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Chemical Property of (1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(4-chloro-3-(phenoxymethyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate

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Technology Process of (1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(4-chloro-3-(phenoxymethyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate

There total 5 articles about (1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(4-chloro-3-(phenoxymethyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-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: 82.0%

: 1416165-43-9
(1S,2S,3S,4R,5S)-5-(4-chloro-3-(phenoxymethyl)phenyl)-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol

: 108-24-7
acetic anhydride

: 1416165-44-0
(1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(4-chloro-3-(phenoxymethyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate

Guidance literature:: With dmap; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 0 - 20 ℃; for 2h; Inert atmosphere;

Reference yield:

: 1416165-38-2
((2R,3R,4S,5R,6S)-6-(4-chloro-3-(phenoxymethyl)phenyl)-6-methoxy-3,4,5-tris((trimethylsilyl)oxy)tetrahydro-2H-pyran-2-yl)methanol

: 1416165-44-0
(1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(4-chloro-3-(phenoxymethyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate

Guidance literature:: Multi-step reaction with 4 steps

1: triethylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 3 h / 0 - 10 °C / Inert atmosphere

2: sodium ethanolate / ethanol / 55 °C / Inert atmosphere

3: trifluoroacetic acid / dichloromethane / 0 - 20 °C / Inert atmosphere

4: dmap; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

With dmap; sodium ethanolate; sulfur trioxide pyridine complex; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; ethanol; dichloromethane; dimethyl sulfoxide;

Reference yield:

: 1416165-40-6
(2S,3R,4S,5R,6S)-6-(4-chloro-3-(phenoxymethyl)phenyl)-6-methoxy-3,4,5-tris((trimethylsilyl)oxy)tetrahydro-2H-pyran-2-carbaldehyde

: 1416165-44-0
(1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(4-chloro-3-(phenoxymethyl)phenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate

Guidance literature:: Multi-step reaction with 3 steps

1: sodium ethanolate / ethanol / 55 °C / Inert atmosphere

2: trifluoroacetic acid / dichloromethane / 0 - 20 °C / Inert atmosphere

3: dmap; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

With dmap; sodium ethanolate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; ethanol; dichloromethane;