ChemicalBook CAS DataBase List (2S,3R,4S,5S)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6,6-bis(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

(2S,3R,4S,5S)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6,6-bis(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol synthesis

5synthesis methods

Product Name:(2S,3R,4S,5S)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6,6-bis(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol
CAS Number:1528636-39-6
Molecular formula:C23H29ClO8
Molecular Weight:468.92

461432-23-5 Synthesis

4-Bromo-1-chloro-2-(4-ethoxybenzyl)benzene

461432-23-5
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(2S,3R,4S,5S)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6,6-bis(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

1528636-39-6
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Yield:-

Steps:

Multi-step reaction with 5 steps
1.1: n-hexyllithium / toluene; tetrahydrofuran; hexane / 1 h / -84 - -74 °C / Large scale
1.2: 2 h / -74 - -15 °C / Large scale
2.1: methanesulfonic acid / toluene; tetrahydrofuran; hexane / 25.83 h / -71 - 20 °C / Large scale
3.1: pyridinium p-toluenesulfonate / dichloromethane; water / 8 h / 20 °C / Large scale
4.1: dimethyl sulfoxide; triethylamine; sulfur trioxide pyridine complex / dichloromethane / 3.75 h / 10 - 12 °C / Large scale
5.1: sodium ethanolate; ethanol / 4.08 h / 55 °C / Large scale
5.2: 0.83 h / 55 °C / Large scale

References:

Bernhardson, David;Brandt, Thomas A.;Hulford, Catherine A.;Lehner, Richard S.;Preston, Brian R.;Price, Kristin;Sagal, John F.;Pierre, Michael J. St.;Thompson, Peter H.;Thuma, Benjamin [Organic Process Research and Development,2014,vol. 18,# 1,p. 57 - 65]

50-00-0 Synthesis