L-proline-(2S,3R,4R,5S,6R)-2-{3-[5-(4-fluoro-phenyl)-thiophen-2-ylmethyl]-4-methyl-phenyl}-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

Base Information

• Chemical Name: L-proline-(2S,3R,4R,5S,6R)-2-{3-[5-(4-fluoro-phenyl)-thiophen-2-ylmethyl]-4-methyl-phenyl}-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol
• CAS No.: 1409936-68-0
• Molecular Formula: C₅H₉NO₂*C₂₄H₂₅FO₅S
• Molecular Weight: 559.656
• Mol file: 1409936-68-0.mol

Synonyms:L-proline-(2S,3R,4R,5S,6R)-2-{3-[5-(4-fluoro-phenyl)-thiophen-2-ylmethyl]-4-methyl-phenyl}-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

Chemical Property of L-proline-(2S,3R,4R,5S,6R)-2-{3-[5-(4-fluoro-phenyl)-thiophen-2-ylmethyl]-4-methyl-phenyl}-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of L-proline-(2S,3R,4R,5S,6R)-2-{3-[5-(4-fluoro-phenyl)-thiophen-2-ylmethyl]-4-methyl-phenyl}-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

There total 5 articles about L-proline-(2S,3R,4R,5S,6R)-2-{3-[5-(4-fluoro-phenyl)-thiophen-2-ylmethyl]-4-methyl-phenyl}-6-hydroxymethyl-tetrahydro-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: 93.0%

canagliflozin (842133-18-0,1589590-87-3) + L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → L-proline-(2S,3R,4R,5S,6R)-2-{3-[5-(4-fluoro-phenyl)-thiophen-2-ylmethyl]-4-methyl-phenyl}-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol (1409936-68-0)

Guidance literature:

In n-heptane; ethyl acetate; at 60 - 65 ℃; for 5h; Solvent; Inert atmosphere;

Reference yield:

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one (32469-28-6,55515-28-1,55515-29-2,32384-65-9) → L-proline-(2S,3R,4R,5S,6R)-2-{3-[5-(4-fluoro-phenyl)-thiophen-2-ylmethyl]-4-methyl-phenyl}-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol (1409936-68-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: n-butyllithium / tetrahydrofuran; toluene; hexane / 1.5 h / -80 - -70 °C

1.2: -80 - -70 °C

1.3: -80 - 20 °C

2.1: n-butyllithium / tetrahydrofuran; toluene; hexane / 1.5 h / -80 - -70 °C

2.2: -80 - -70 °C

2.3: -80 - 20 °C

3.1: triethylsilane / dichloromethane; acetonitrile / 1 h / -55 - -40 °C / Inert atmosphere

3.2: 2 h / -55 - -40 °C

4.1: ethyl acetate; n-heptane / 5 h / 60 - 65 °C / Inert atmosphere

With triethylsilane; n-butyllithium; In tetrahydrofuran; hexane; n-heptane; dichloromethane; ethyl acetate; toluene; acetonitrile;

Reference yield:

2-allyloxy-2-{3-[5-(4-fluoro-phenyl)-thiophen-2-ylmethyl]-4-methyl-phenyl}-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol → L-proline-(2S,3R,4R,5S,6R)-2-{3-[5-(4-fluoro-phenyl)-thiophen-2-ylmethyl]-4-methyl-phenyl}-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol (1409936-68-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran; toluene; hexane / 1.5 h / -80 - -70 °C

1.2: -80 - -70 °C

1.3: -80 - 20 °C

2.1: triethylsilane / dichloromethane; acetonitrile / 1 h / -55 - -40 °C / Inert atmosphere

2.2: 2 h / -55 - -40 °C

3.1: ethyl acetate; n-heptane / 5 h / 60 - 65 °C / Inert atmosphere

With triethylsilane; n-butyllithium; In tetrahydrofuran; hexane; n-heptane; dichloromethane; ethyl acetate; toluene; acetonitrile;

upstream raw materials:

canagliflozin

L-proline

3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-one

(3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one