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

Base Information

• Chemical Name: (2R,3R,4R,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
• CAS No.: 1373321-04-0
• Molecular Formula: C₂₁H₂₅ClO₆
• Molecular Weight: 408.879
• Mol file: 1373321-04-0.mol

Synonyms:

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

Chemical Property:

• Boiling Point: 609.0±55.0 °C(Predicted)
• Density: 1.349±0.06 g/cm3(Predicted)

Purity/Quality:

NLT 98% ^*data from raw suppliers

1R-Dapagliflozin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: 1R-Dapagliflozin is an isomer of Dapagliflozin (D185370), which is a sodium-glucose transporter 2 inhibitor.

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

There total 134 articles about (2R,3R,4R,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-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: 100.0%

(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-ethoxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (461432-25-7) → dapagliflozin (461432-26-8,1373321-04-0)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; ethanol;

DOI:10.1021/jm701272q

Reference yield: 98.83%

2-chloro-5-(2,3,4,6-tetra-O-trimethylsilyl-D-glucopyranose-1-yl)-4'-ethoxydiphenylmethane → dapagliflozin (461432-26-8,1373321-04-0)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; methanol; water; at 0 - 20 ℃; for 7h; Temperature;

Reference yield: 98.7%

C21H25ClO6*C3H8O2 → dapagliflozin (461432-26-8,1373321-04-0)

Guidance literature:

In n-heptane; tert-butyl methyl ether; at -15 - 50 ℃; Inert atmosphere;

upstream raw materials:

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

(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-ethoxybenzyl)phenyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

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

2-chloro-5-iodobenzoylchloride

Downstream raw materials:

(2R,4R,5S,6S)-4,5-bis(benzyloxy)-2-(benzyloxymethyl)-6-(4-chloro-3-(4-ethoxybenzyl)phenyl)dihydro-2H-pyran-3(4H)-one