1,4-dihydroxy-3-((2R,3R,5S,6R)-6-((R)-1-methylpropyl)-3,5-dimethyltetrahydro-2H-pyran-2-yl)-5-phenylpyridin-2(1H)-one

Base Information

• Chemical Name: 1,4-dihydroxy-3-((2R,3R,5S,6R)-6-((R)-1-methylpropyl)-3,5-dimethyltetrahydro-2H-pyran-2-yl)-5-phenylpyridin-2(1H)-one
• CAS No.: 1234619-27-2
• Molecular Formula: C₂₂H₂₉NO₄
• Molecular Weight: 371.477
• Mol file: 1234619-27-2.mol

Synonyms:

Chemical Property of 1,4-dihydroxy-3-((2R,3R,5S,6R)-6-((R)-1-methylpropyl)-3,5-dimethyltetrahydro-2H-pyran-2-yl)-5-phenylpyridin-2(1H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,4-dihydroxy-3-((2R,3R,5S,6R)-6-((R)-1-methylpropyl)-3,5-dimethyltetrahydro-2H-pyran-2-yl)-5-phenylpyridin-2(1H)-one

There total 2 articles about 1,4-dihydroxy-3-((2R,3R,5S,6R)-6-((R)-1-methylpropyl)-3,5-dimethyltetrahydro-2H-pyran-2-yl)-5-phenylpyridin-2(1H)-one 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:

(S)-3-((E,4S,5R,6R)-5-(hydroxy)-2,4,6-trimethyloct-2-enoyl)-4-isopropyloxazolidin-2-one (1442693-34-6) → 1,4-dihydroxy-3-((2R,3R,5S,6R)-6-((R)-1-methylpropyl)-3,5-dimethyltetrahydro-2H-pyran-2-yl)-5-phenylpyridin-2(1H)-one (1234619-27-2) + C22H29NO4 (1442693-53-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: ammonia; lithium / tetrahydrofuran / 0.05 h / -78 °C

1.2: 4 h / 30 °C

2.1: diisobutylaluminium hydride / dichloromethane; hexane / 0.5 h / -78 °C

2.2: 20 h / Reflux

With ammonia; lithium; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane; 1.1: |Birch Reduction / 2.2: |Knoevenagel Condensation;

DOI:10.1021/ol401406m

Reference yield:

(S)-3-((2E,6E)-(4S,5S)-5-Hydroxy-2,4,6-trimethyl-octa-2,6-dienoyl)-4-isopropyl-oxazolidin-2-one → 1,4-dihydroxy-3-((2R,3R,5S,6R)-6-((R)-1-methylpropyl)-3,5-dimethyltetrahydro-2H-pyran-2-yl)-5-phenylpyridin-2(1H)-one (1234619-27-2) + C22H29NO4 (1442693-53-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: hydrogen; [(1,5-cyclooctadiene)Rh(PPh₃)2]PF₆ / 1,2-dichloro-ethane / 12 h / -10 °C

2.1: ammonia; lithium / tetrahydrofuran / 0.05 h / -78 °C

2.2: 4 h / 30 °C

3.1: diisobutylaluminium hydride / dichloromethane; hexane / 0.5 h / -78 °C

3.2: 20 h / Reflux

With [(1,5-cyclooctadiene)Rh(PPh₃)2]PF₆; ammonia; hydrogen; lithium; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane; 1,2-dichloro-ethane; 2.1: |Birch Reduction / 3.2: |Knoevenagel Condensation;

DOI:10.1021/ol401406m

Reference yield:

1,4-dihydroxy-3-((2R,3R,5S,6R)-6-((R)-1-methylpropyl)-3,5-dimethyltetrahydro-2H-pyran-2-yl)-5-phenylpyridin-2(1H)-one (1234619-27-2) + methyl iodide (74-88-4) → N-(O-methyl)-septoriamycin A (1234619-28-3)

Guidance literature:

With caesium carbonate; In acetone; at 20 ℃; for 5h;

DOI:10.1021/np200940b

upstream raw materials:

(S)-3-((E,4S,5R,6R)-5-(hydroxy)-2,4,6-trimethyloct-2-enoyl)-4-isopropyloxazolidin-2-one

Downstream raw materials:

C₂₄H₃₃NO₄

C₂₄H₃₃NO₄

C₂₄H₃₃NO₄

N-(O-methyl)-septoriamycin A