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

Base Information

• Chemical 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 No.: 1528636-39-6
• Molecular Formula: C23H29ClO8
• Molecular Weight: 468.931
• Mol file: 1528636-39-6.mol

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

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

Chemical Property:

• Boiling Point: 651.3±55.0 °C(Predicted)
• PKA: 12.47±0.70(Predicted)
• PSA: 128.84000
• Density: 1.42±0.1 g/cm3(Predicted)
• LogP: 0.96500

Purity/Quality:

99%, ^*data from raw suppliers

(2S,3R,4S,5S)-2-(4-Chloro-3-(4-ethoxybenzyl)phenyl)-6,6-bis(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (2S,3R,4S,5S)-2-(4-Chloro-3-(4-ethoxybenzyl)phenyl)-6,6-bis(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol is an antidiabetic agent and an Ertugliflozin (1210344-57-2) intermediate.

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

There total 8 articles about (2S,3R,4S,5S)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6,6-bis(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-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: 35.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + C22H25ClO7 → (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)

Guidance literature:

With sodium ethanolate; In ethanol; at 55 ℃; for 4h;

Reference yield:

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (2S,3R,4S,5R,6S)-6-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-methoxy-3,4,5-tris-(trimethylsilyloxy)tetrahydro-2H-pyran-2-carbaldehyde (1528636-33-0) → (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)

Guidance literature:

formaldehyd; (2S,3R,4S,5R,6S)-6-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-methoxy-3,4,5-tris-(trimethylsilyloxy)tetrahydro-2H-pyran-2-carbaldehyde; With ethanol; sodium ethanolate; at 55 ℃; for 4.08333h; Large scale;

With sodium hydrogen sulfate; water; at 55 ℃; for 0.833333h; Large scale;

DOI:10.1021/op400289z

Reference yield:

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol (714269-57-5) → (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)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 1H-imidazole / dichloromethane / 1 h / 5 - 20 °C / Large scale

2.1: pyridinium p-toluenesulfonate / dichloromethane; water / 8 h / 20 °C / Large scale

3.1: dimethyl sulfoxide; triethylamine; sulfur trioxide pyridine complex / dichloromethane / 3.75 h / 10 - 12 °C / Large scale

4.1: sodium ethanolate; ethanol / 4.08 h / 55 °C / Large scale

4.2: 0.83 h / 55 °C / Large scale

With 1H-imidazole; ethanol; sodium ethanolate; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; In dichloromethane; water;

DOI:10.1021/op400289z

upstream raw materials:

C₃₄H₅₉ClO₇Si₄

(2S,3R,4S,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-(hydroxymethyl)-2-methoxy-tetrahydropyran-3,4,5-triol

formaldehyd

(2S,3R,4S,5R,6S)-6-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-methoxy-3,4,5-tris-(trimethylsilyloxy)tetrahydro-2H-pyran-2-carbaldehyde

Downstream raw materials:

Ertugliflozin

(1S,2S,3S,4R,5S)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol (1:1) compound with (S)-5-oxopyrrolidine-2-carboxylic acid