(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

Base Information

Chemical Name:(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
CAS No.:1416165-21-3
Molecular Formula:C₂₃H₂₅ClO₇
Molecular Weight:448.9
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 6 articles about (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 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:

: 1416165-20-2
(2S,3R,4S,5S)-2-(3-(4-(allyloxy)benzyl)-4-chlorophenyl)-6,6-bis(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

: 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

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 1h;

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 6 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

With n-butyllithium; sodium ethanolate; caesium carbonate; 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

: 1416165-21-3
(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

Guidance literature:: Multi-step reaction with 4 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

With sodium ethanolate; trifluoroacetic acid; In ethanol; dichloromethane; dimethyl sulfoxide;