4-Methyl-benzenesulfinic acid ((1R,3R)-1,3-di-furan-2-yl-3-hydroxy-propyl)-amide

Base Information

• Chemical Name: 4-Methyl-benzenesulfinic acid ((1R,3R)-1,3-di-furan-2-yl-3-hydroxy-propyl)-amide
• CAS No.: 729567-28-6
• Molecular Formula: C₁₈H₁₉NO₄S
• Molecular Weight: 345.419
• Mol file: 729567-28-6.mol

Synonyms:4-Methyl-benzenesulfinic acid ((1R,3R)-1,3-di-furan-2-yl-3-hydroxy-propyl)-amide

Chemical Property of 4-Methyl-benzenesulfinic acid ((1R,3R)-1,3-di-furan-2-yl-3-hydroxy-propyl)-amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Methyl-benzenesulfinic acid ((1R,3R)-1,3-di-furan-2-yl-3-hydroxy-propyl)-amide

There total 4 articles about 4-Methyl-benzenesulfinic acid ((1R,3R)-1,3-di-furan-2-yl-3-hydroxy-propyl)-amide 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: 51.0%

4-Methyl-benzenesulfinic acid ((R)-1,3-di-furan-2-yl-3-oxo-propyl)-amide (729567-21-9) → (E)-1,3-Di-furan-2-yl-prop-2-en-1-ol (937167-70-9) + 4-Methyl-benzenesulfinic acid ((1R,3S)-1,3-di-furan-2-yl-3-hydroxy-propyl)-amide (729567-27-5) + 4-Methyl-benzenesulfinic acid ((1R,3R)-1,3-di-furan-2-yl-3-hydroxy-propyl)-amide (729567-28-6)

Guidance literature:

With NaHB₄; In tetrahydrofuran; at 25 ℃;

DOI:10.1055/s-2004-820050

Reference yield: 44.0%

4-Methyl-benzenesulfinic acid ((R)-1,3-di-furan-2-yl-3-oxo-propyl)-amide (729567-21-9) → 4-Methyl-benzenesulfinic acid ((1R,3S)-1,3-di-furan-2-yl-3-hydroxy-propyl)-amide (729567-27-5) + 4-Methyl-benzenesulfinic acid ((1R,3R)-1,3-di-furan-2-yl-3-hydroxy-propyl)-amide (729567-28-6)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 25 ℃; for 1.5h; Further Variations:; Reagents; Solvents; Temperatures; Product distribution;

DOI:10.1055/s-2004-820050

Reference yield:

furfural (98-01-1) → 4-Methyl-benzenesulfinic acid ((1R,3R)-1,3-di-furan-2-yl-3-hydroxy-propyl)-amide (729567-28-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 98 percent / Ti(OEt)4

2.1: LiHMDS / tetrahydrofuran / 0.5 h / -78 °C

2.2: 87 percent / tetrahydrofuran / 1 h / -78 °C

3.1: 24 percent / NaHB₄ / tetrahydrofuran / 25 °C

With titanium(IV) tetraethanolate; lithium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.1055/s-2004-820050

upstream raw materials:

4-Methyl-benzenesulfinic acid ((R)-1,3-di-furan-2-yl-3-oxo-propyl)-amide

furfural

(S)-p-toluenesulfinimide

Downstream raw materials:

6-methoxy-2-(6-methoxy-3-oxo-3,6-dihydro-2H-pyran-2-ylmethyl)-1-(toluene-4-sulfonyl)-1,6-dihydro-2H-pyridin-3-one

(2R,3R,6S)-6-Allyl-2-((2R,3S,6S)-3-hydroxy-6-methoxy-3,6-dihydro-2H-pyran-2-ylmethyl)-1-(toluene-4-sulfonyl)-1,2,3,6-tetrahydro-pyridin-3-ol

6-allyl-2-(6-methoxy-3-oxo-3,6-dihydro-2H-pyran-2-ylmethyl)-1-(toluene-4-sulfonyl)-1,6-dihydro-2H-pyridin-3-one