4H-Pyran-4-one,2,3-dihydro-2-methyl-,(2R)-(9CI)

Base Information

• Chemical Name: 4H-Pyran-4-one,2,3-dihydro-2-methyl-,(2R)-(9CI)
• CAS No.: 190912-17-5
• Molecular Formula: C6H8 O2
• Molecular Weight: 112.13
• Mol file: 190912-17-5.mol

Synonyms:4H-Pyran-4-one,2,3-dihydro-2-methyl-, (R)-

Chemical Property of 4H-Pyran-4-one,2,3-dihydro-2-methyl-,(2R)-(9CI)

Chemical Property:

• Boiling Point: 155.4±15.0 °C(Predicted)
• PSA: 26.30000
• Density: 1.045±0.06 g/cm3(Predicted)
• LogP: 0.87800

Purity/Quality:

97% ^*data from raw suppliers

(R)-2-Methyl-2H-pyran-4(3H)-one 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4H-Pyran-4-one,2,3-dihydro-2-methyl-,(2R)-(9CI)

There total 5 articles about 4H-Pyran-4-one,2,3-dihydro-2-methyl-,(2R)-(9CI) 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: 61.0%

acetaldehyde (75-07-0,9002-91-9) + (E)-triethyl((4-methoxybuta-1,3-dien-2-yl)oxy)silane → (R)-2-methyl-2,3-dihydro-4H-pyran-4-one (190912-17-5,190912-15-3)

Guidance literature:

acetaldehyde; (E)-triethyl((4-methoxybuta-1,3-dien-2-yl)oxy)silane; With CrCl(C₆H₂(O)(C₁₀H₁₅)(CH₃)(CHNC₉H₈O)); at -20 ℃; for 15h; Molecular sieve;

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1002/anie.202016477

Reference yield: 61.0%

2-triethylsiloxy-4-methoxy-1,3-butadiene (1085182-72-4) + acetaldehyde (75-07-0,9002-91-9) → (R)-2-methyl-2,3-dihydro-4H-pyran-4-one (190912-17-5,190912-15-3)

Guidance literature:

2-triethylsiloxy-4-methoxy-1,3-butadiene; acetaldehyde; With CrCl(C₆H₂(O)(C₁₀H₁₅)(CH₃)(CHNC₉H₈O)); at -20 - 20 ℃; Inert atmosphere; Schlenk technique;

With trifluoroacetic acid; In dichloromethane; Inert atmosphere; Schlenk technique;

DOI:10.1002/chem.202104400

Reference yield: 46.0%

(R)-5-((tert-butyldimethylsilyl)oxy)hex-1-en-3-one (869293-25-4) → (R)-2-methyl-2,3-dihydro-4H-pyran-4-one (190912-17-5,190912-15-3)

Guidance literature:

With dichloro bis(acetonitrile) palladium(II); p-benzoquinone; In water; acetone; at 45 - 50 ℃; Large scale;

DOI:10.1021/op500135x

upstream raw materials:

(E)-5-((R)-tert-butyldimethylsilyloxy)-1-(piperidin-1-ylimino)hexan-3-one

(R)-5-((tert-butyldimethylsilyl)oxy)hex-1-en-3-one

acetaldehyde

2-triethylsiloxy-4-methoxy-1,3-butadiene

Downstream raw materials:

(2R,6R)-2,6-dimethyldihydro-2H-pyran-4(3H)-one

(2R,6S)-2,6-dimethyltetrahydro-4H-pyran-4-one

(2R)-2-methyltetrahydro-4H-pyran-4-one

dimethyl (4,4'-biphenyldiylbis(1H-imidazole-4,2-diyl((2S)-2,1-pyrrolidinediyl)((1S)-1-((2R,6R)-2,6-dimethyltetrahydro-2H-pyran-4-yl)-2-oxo-2,1-ethanediyl)))biscarbamate

Refernces

• 1、 Sp?th, Georg,Fürstner, Alois. "Scalable De Novo Synthesis of Aldgarose and Total Synthesis of Aldgamycin N". supporting information. p. 7900 - 7905. Retrieved 2021/03/08.
• 2、 -. "HEPATITIS C VIRUS INHIBITORS". Page/Page column 35-36. . Retrieved 2012/08/28.