(19S,20S)-19-(furan-3-yl)-12-hydroxy-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.02,7.02,10.014,16.014,20]docosane-5,17-dione

Base Information

• Chemical Name: (19S,20S)-19-(furan-3-yl)-12-hydroxy-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.02,7.02,10.014,16.014,20]docosane-5,17-dione
• CAS No.: 989-61-7
• Molecular Formula: C₂₆H₃₂O₈
• Molecular Weight: 472.535
• DSSTox Substance ID: DTXSID00912997
• Mol file: 989-61-7.mol

Synonyms:LIMONOL;989-61-7;DTXSID00912997;AKOS032948444;12-(Furan-3-yl)-8-hydroxy-6,6,8a,12a-tetramethyldodecahydro-1H,3H-oxireno[c]pyrano[4'',3'':2',3']furo[3',4':5,6]naphtho[1,2-d]pyran-3,10(9aH)-dione

Chemical Property of (19S,20S)-19-(furan-3-yl)-12-hydroxy-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.02,7.02,10.014,16.014,20]docosane-5,17-dione

Chemical Property:

• Melting Point: 318-320 °C
• Boiling Point: 675.8°Cat760mmHg
• PKA: 14.51±0.70(Predicted)
• Flash Point: 362.5°C
• PSA: 107.73000
• Density: 1.39g/cm³
• LogP: 2.92920
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 1
• Exact Mass: 472.20971797
• Heavy Atom Count: 34
• Complexity: 964

Purity/Quality:

98%Min ^*data from raw suppliers

Limonol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2CC(C3(C(C24COC(=O)CC4O1)CCC5(C36C(O6)C(=O)OC5C7=COC=C7)C)C)O)C
• Isomeric SMILES: C[C@@]12CCC3C(C14C(O4)C(=O)O[C@H]2C5=COC=C5)(C(CC6C37COC(=O)CC7OC6(C)C)O)C

Technology Process of (19S,20S)-19-(furan-3-yl)-12-hydroxy-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.02,7.02,10.014,16.014,20]docosane-5,17-dione

There total 5 articles about (19S,20S)-19-(furan-3-yl)-12-hydroxy-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.02,7.02,10.014,16.014,20]docosane-5,17-dione 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: 76.0%

Limonin (1180-71-8,42867-83-4) → 7α-limonol (989-61-7) + 7β-limonol (1258-86-2)

Guidance literature:

With methanol; sodium tetrahydroborate; In dichloromethane; at -20 ℃; for 0.25h;

DOI:10.1002/anie.202104228

Reference yield: 14.0%

limonol phenyl selenocarbonate → 7α-limonol (989-61-7) + 7-deoxolimonin + limonol formate

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In 1,3,5-trimethyl-benzene; for 0.5h; Heating;

DOI:10.1002/hlca.19810640516

Reference yield:

C27H31ClO9 → 7α-limonol (989-61-7)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / benzene / 1 h

2: 2 percent / Bu₃SnH, azo-bis(isobutyronitrile) / 1,3,5-trimethyl-benzene / 0.5 h / Heating

With pyridine; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In 1,3,5-trimethyl-benzene; benzene;

DOI:10.1002/hlca.19810640516

upstream raw materials:

Limonin

Refernces

• 1、 Furiassi, Lucia,Hergenrother, Paul J.,Tonogai, Emily J.. "Limonin as a Starting Point for the Construction of Compounds with High Scaffold Diversity". supporting information. p. 16119 - 16128. Retrieved 2021/06/14.
• 2、 Wada,Yagi,Kurihara,Haga. "Studies on the constituents of edible and medicinal plants. III. Effects of seven limonoids on the sleeping time induced in mice by anesthetics". . p. 3079 - 3080. Retrieved 2007/10/02.