(2S,3R,4S,5S,6R)-2-(4-Chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol (CAS No. 714269-57-5)

(2S,3R,4S,5S,6R)-2-(4-Chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol (CAS No. 714269-57-5)

(2S,3R,4S,5S,6R)-2-(4-Chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol (CAS No. 714269-57-5) is a synthetic compound that serves as an intermediate in the production of dapagliflozin, a medication used to treat type 2 diabetes. This compound is characterized by its unique stereochemistry and functional groups that contribute to its biological activity.

Chemical and Physical Properties

• CAS Number: 714269-57-5
• MDL Number: MFCD27923102
• EINECS: 615-293-6
• Molecular Formula: C₂₂H₂₇ClO₇
• Molecular Weight: 438.90 g/mol
• Boiling Point: 609.6 ± 55.0 °C (predicted)
• Melting Point: >80°C (decomposes)
• Density: 1.39 ± 0.1 g/cm³ at 20 °C (760 Torr)
• Appearance: White solid

Structure and Composition

The structure of (2S,3R,4S,5S,6R)-2-(4-Chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol features a tetrahydropyran ring with multiple hydroxyl groups and a methoxy group. The presence of a chloro substituent and an ethoxybenzyl group enhances its biological activity and solubility.

Biological Activity and Applications

1. Antidiabetic Agent: As an intermediate in the synthesis of dapagliflozin, this compound plays a crucial role in glucose regulation by inhibiting sodium-glucose cotransporter 2 (SGLT2), thereby promoting glucose excretion in urine.
2. Research Applications: It is utilized in pharmaceutical research to develop and optimize SGLT2 inhibitors for better efficacy and safety profiles in diabetes management.

Safety and Handling

The compound is classified with potential hazards:

• H302: Harmful if swallowed
• H315: Causes skin irritation
• H319: Causes serious eye irritation
  Handling should be done with appropriate personal protective equipment (PPE) to avoid exposure.

Storage Recommendations

For long-term stability, store the compound at temperatures between 2–8°C in a cool, dry place away from light.

In summary, (2S,3R,4S,5S,6R)-2-(4-Chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol is an important intermediate in the development of antidiabetic drugs with significant therapeutic potential.

Citations:

1. https://www.lgcstandards.com/LU/en/-2S-3R-4S-5S-6R-2-4-Chloro-3-4-ethoxybenzyl-phenyl-6-hydroxymethyl-2-methoxy-tetrahydropyran-3-4-5-triol/p/MM3611.03
2. https://www.chemsrc.com/en/cas/714269-57-5_730037.html
3. https://www.chemicalbook.com/ChemicalProductProperty_EN_CB72610561.htm
4. https://pubchem.ncbi.nlm.nih.gov/compound/24807437
5. https://www.ambeed.com/products/714269-57-5.html
6. https://www.chemicalbook.com/CASEN_714269-57-5.htm
7. https://www.bldpharm.com/products/714269-57-5.html
8. https://www.unibestpharm.com/CAS-No-714269-57-5-2S-3R-4S-5S-6R-2-4-chloro-3-4-ethoxybenzyl-phenyl-6-hydroxyMethyl-2-Methoxytetrahydro-2H-pyran-3-4-5-triol-pd41611330.html