2H-Pyran-2-one, 5,6-dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-, (5R-cis)-

Base Information

• Chemical Name: 2H-Pyran-2-one, 5,6-dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-, (5R-cis)-
• CAS No.: 52247-81-1
• Molecular Formula: C₁₄H₁₆O₄
• Molecular Weight: 248.279
• UNII: RUH8AF5DWD
• DSSTox Substance ID: DTXSID801150000
• Nikkaji Number: J89.687J
• Wikidata: Q105287158
• Mol file: 52247-81-1.mol

Synonyms:(+)-Dihydrokawain-5-ol;(2S,3R)-3-hydroxy-4-methoxy-2-(2-phenylethyl)-2,3-dihydropyran-6-one;(5R,6S)-5,6-Dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-2H-pyran-2-one;52247-81-1;2H-Pyran-2-one, 5,6-dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-, (5R-cis)-;RUH8AF5DWD;7,8-Dihydrokawain-5-ol;(+)- Dihydrokawain-5-ol;Dihydrokawain-5-ol, (+)-;MEGxp0_001720;ACon1_000142;CHEBI:181514;DTXSID801150000;(+)-(5R,6S)-Dihydrokawain-5-ol;AKOS040734799;NCGC00180841-01;BRD-K90768238-001-01-0;2H-Pyran-2-one, 5,6-dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-, (5R,6S)-

Chemical Property of 2H-Pyran-2-one, 5,6-dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-, (5R-cis)-

Chemical Property:

• Melting Point: 89.5-90 °C(Solv: ethyl ether (60-29-7))
• Boiling Point: 472.3±45.0 °C(Predicted)
• PKA: 11.36±0.60(Predicted)
• Density: 1.21±0.1 g/cm3(Predicted)
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 248.10485899
• Heavy Atom Count: 18
• Complexity: 318

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=CC(=O)OC(C1O)CCC2=CC=CC=C2
• Isomeric SMILES: COC1=CC(=O)O[C@H]([C@H]1O)CCC2=CC=CC=C2

Technology Process of 2H-Pyran-2-one, 5,6-dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-, (5R-cis)-

There total 16 articles about 2H-Pyran-2-one, 5,6-dihydro-5-hydroxy-4-methoxy-6-(2-phenylethyl)-, (5R-cis)- 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: 92.0%

(5R,6S)-4-methoxy-5-(4-methoxybenzyloxy)-6-(1-phenylethyl)-5,6-dihydro-2H-pyran-2-one (259142-63-7) → (5R,6S)-5-hydroxy-4-methoxy-6-phenethyl-5,6-dihydro-2H-pyran-2-one (52247-81-1)

Guidance literature:

With phosphate buffer; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 20 ℃; pH=7;

DOI:10.1021/jo049858n

Reference yield: 90.0%

(5R,6S)-4-Methoxy-5-methoxymethoxy-6-phenethyl-5,6-dihydro-pyran-2-one → (+/-)-dihydrokawain-5-ol (28521-91-7,40864-20-8,41002-32-8,41002-33-9,52247-81-1,56083-47-7,78376-49-5)

Guidance literature:

With sulfuric acid; acetic acid; at 70 ℃; for 3h;

DOI:10.1021/jo961653u

Reference yield:

(5R,6S)-5-(benzyloxy)-4-methoxy-6-phenethyl-5,6-dihydro-2H-2-pyranone (955361-56-5) → (5R,6S)-5-hydroxy-4-methoxy-6-phenethyl-5,6-dihydro-2H-pyran-2-one (52247-81-1)

Guidance literature:

With titanium tetrachloride; In dichloromethane; at 0 ℃; for 0.25h;

DOI:10.1016/j.tetasy.2007.07.032

upstream raw materials:

(5R,6S)-4-methoxy-5-(4-methoxybenzyloxy)-6-(1-phenylethyl)-5,6-dihydro-2H-pyran-2-one

(5S,6R)-5-(benzyloxy)-4-methoxy-6-phenethyl-5,6-dihydro-2H-2-pyranone

(5R,6S)-5-(benzyloxy)-4-methoxy-6-phenethyl-5,6-dihydro-2H-2-pyranone

(4S,5R)-4-benzyloxy-5-(4-methoxybenzyloxy)-3-oxo-7-phenylheptanoic acid ethyl ester

Refernces

Total synthesis of (±)-dihydrokawain-5-ol. Regioselective monoprotection of vicinal syn-diols derived from the iodocyclofunctionalization of α-allenic alcohols

10.1021/jo961653u

The study focuses on the total synthesis of (±)-dihydrokawain-5-ol, a unique natural product isolated from the kava plant (Piper methysticum). The synthesis begins with a highly diastereoselective iodocyclofunctionalization of α-allenic alcohols to produce vinyl iodo syn-vicinal diols. A key feature of the synthesis is the differentiation of the alcohol groups in the vicinal diols through selective monoprotection using methoxymethyl (MOM) ethers or silyl ethers, followed by further functional group manipulations. The work explores various regioselective monoprotection techniques, cyclization strategies, and the isomerization of intermediates to form the final dihydropyranone structure found in dihydrokawain-5-ol. The study exemplifies the challenges and solutions in synthesizing complex natural products with specific stereochemical requirements.