(1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(3-(4-(allyloxy)benzyl)-4-chlorophenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate

Base Information

Chemical Name:(1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(3-(4-(allyloxy)benzyl)-4-chlorophenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate
CAS No.:1416165-22-4
Molecular Formula:C₃₁H₃₃ClO₁₁
Molecular Weight:617.049
Hs Code.:

Synonyms:(1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(3-(4-(allyloxy)benzyl)-4-chlorophenyl)-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-(3-(4-(allyloxy)benzyl)-4-chlorophenyl)-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-(3-(4-(allyloxy)benzyl)-4-chlorophenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate

There total 7 articles about (1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(3-(4-(allyloxy)benzyl)-4-chlorophenyl)-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:

: 1416165-21-3
(1S,2S,3S,4R,5S)-5-(3-(4-(allyloxy)benzyl)-4-chlorophenyl)-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol

: 108-24-7
acetic anhydride

: 1416165-22-4
(1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(3-(4-(allyloxy)benzyl)-4-chlorophenyl)-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 1h;

Reference yield:

: 864070-18-8
4-(5-bromo-2-chlorobenzyl)phenol

: 1416165-22-4
(1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(3-(4-(allyloxy)benzyl)-4-chlorophenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate

Guidance literature:: Multi-step reaction with 7 steps

1.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 0 - 20 °C

2.1: n-butyllithium / tetrahydrofuran; hexanes / 0.5 h / -78 °C / Inert atmosphere

2.2: 3 h / -78 °C

2.3: 16 h / 20 °C

3.1: leutidine / 12 h / 0 - 20 °C

4.1: collidine / dimethyl sulfoxide / 0.75 h / 150 °C

5.1: sodium ethanolate / ethanol / 20 h / 55 °C

5.2: 0.33 h

6.1: trifluoroacetic acid / dichloromethane / 1 h / 0 - 20 °C

7.1: dmap; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 0 - 20 °C

With dmap; n-butyllithium; sodium ethanolate; caesium carbonate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; hexanes; ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

Reference yield:

: 1416165-17-7
(2S,3R,4S,5S,6R)-2-(3-(4-(allyloxy)benzyl)-4-chlorophenyl)-6-(hydroxy methyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

: 1416165-22-4
(1R,2S,3S,4R,5S)-1-(acetoxymethyl)-5-(3-(4-(allyloxy)benzyl)-4-chlorophenyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triyl triacetate

Guidance literature:: Multi-step reaction with 5 steps

1.1: leutidine / 12 h / 0 - 20 °C

2.1: collidine / dimethyl sulfoxide / 0.75 h / 150 °C

3.1: sodium ethanolate / ethanol / 20 h / 55 °C

3.2: 0.33 h

4.1: trifluoroacetic acid / dichloromethane / 1 h / 0 - 20 °C

5.1: dmap; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 0 - 20 °C

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