1H,7H-Naphtho(1,8-bc:4,4a-c')difuran-5,10a(8H)-dicarboxylic acid, 10-(acetyloxy)octahydro-3,5-dihydroxy-4-methyl-8-(((2E)-2-methyl-1-oxo-2-butenyl)oxy)-4-((1aR,2S,3aS,6aS,7S,7aS)-3a,6a,7,7a-tetrahydro-6a-hydroxy-7a-methyl-2,7-methanofuro(2,3-b)oxireno(e)oxepin-1a(2H)-yl)-, dimethyl ester, (2aR,3S,4S,4aR,5S,7aS,8R,10R,10aS,10bR)-

Base Information

• Chemical Name: 1H,7H-Naphtho(1,8-bc:4,4a-c')difuran-5,10a(8H)-dicarboxylic acid, 10-(acetyloxy)octahydro-3,5-dihydroxy-4-methyl-8-(((2E)-2-methyl-1-oxo-2-butenyl)oxy)-4-((1aR,2S,3aS,6aS,7S,7aS)-3a,6a,7,7a-tetrahydro-6a-hydroxy-7a-methyl-2,7-methanofuro(2,3-b)oxireno(e)oxepin-1a(2H)-yl)-, dimethyl ester, (2aR,3S,4S,4aR,5S,7aS,8R,10R,10aS,10bR)-
• CAS No.: 95507-03-2
• Molecular Formula: C₃₅H₄₄O₁₆
• Molecular Weight: 720.725
• European Community (EC) Number: 619-136-2
• DSSTox Substance ID: DTXSID30896892
• Mol file: 95507-03-2.mol

Synonyms:95507-03-2;Dimethyl (4S,5S,6S,7S,8R,11S,12R,14R,15S)-12-acetyloxy-4,7-dihydroxy-6-[(1R,2S,6S,9R,11S)-2-hydroxy-11-methyl-5,7,10-trioxatetracyclo[6.3.1.02,6.09,11]dodec-3-en-9-yl]-6-methyl-14-[(E)-2-methylbut-2-enoyl]oxy-3,9-dioxatetracyclo[6.6.1.01,5.011,15]pentadecane-4,11-dicarboxylate;C35-H44-O16;1H,7H-Naphtho(1,8-bc:4,4a-c')difuran-5,10a(8H)-dicarboxylic acid, 10-(acetyloxy)octahydro-3,5-dihydroxy-4-methyl-8-(((2E)-2-methyl-1-oxo-2-butenyl)oxy)-4-((1aR,2S,3aS,6aS,7S,7aS)-3a,6a,7,7a-tetrahydro-6a-hydroxy-7a-methyl-2,7-methanofuro(2,3-b)oxireno(e)oxepin-1a(2H)-yl)-, dimethyl ester, (2aR,3S,4S,4aR,5S,7aS,8R,10R,10aS,10bR)-;1H,7H-Naphtho[1,8-bc:4,4a-c']difuran-5,10a(8H)-dicarboxylic acid, 10-(acetyloxy)octahydro-3,5-dihydroxy-4-methyl-8-[[(2E)-2-methyl-1-oxo-2-butenyl]oxy]-4-[(1aR,2S,3aS,6aS,7S,7aS)-3a,6a,7,7a-tetrahydro-6a-hydroxy-7a-methyl-2,7-methanofuro[2,3-b]oxireno[e]oxepin-1a(2H)-yl]-, dimethyl ester, (2aR,3S,4S,4aR,5S,7aS,8R,10R,10aS,10bR)-;SCHEMBL5933479;DTXSID30896892

Chemical Property of 1H,7H-Naphtho(1,8-bc:4,4a-c')difuran-5,10a(8H)-dicarboxylic acid, 10-(acetyloxy)octahydro-3,5-dihydroxy-4-methyl-8-(((2E)-2-methyl-1-oxo-2-butenyl)oxy)-4-((1aR,2S,3aS,6aS,7S,7aS)-3a,6a,7,7a-tetrahydro-6a-hydroxy-7a-methyl-2,7-methanofuro(2,3-b)oxireno(e)oxepin-1a(2H)-yl)-, dimethyl ester, (2aR,3S,4S,4aR,5S,7aS,8R,10R,10aS,10bR)-

Chemical Property:

• Vapor Pressure: 5.01E-29mmHg at 25°C
• Boiling Point: 792.4°C at 760 mmHg
• Flash Point: 244.8°C
• PSA: 215.34000
• Density: 1.51g/cm³
• LogP: -0.20310
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 16
• Rotatable Bond Count: 10
• Exact Mass: 720.26293531
• Heavy Atom Count: 51
• Complexity: 1660

Purity/Quality:

99% ^*data from raw suppliers

AZADIRACHTIN B 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC=C(C)C(=O)OC1CC(C2(COC3C2C14COC(C4C(C3O)(C)C56C7CC(C5(O6)C)C8(C=COC8O7)O)(C(=O)OC)O)C(=O)OC)OC(=O)C
• Isomeric SMILES: C/C=C(\C)/C(=O)O[C@@H]1C[C@H]([C@]2(CO[C@@H]3[C@H]2C14CO[C@@]([C@@H]4[C@]([C@@H]3O)(C)[C@@]56C7C[C@@H]([C@@]5(O6)C)[C@]8(C=CO[C@H]8O7)O)(C(=O)OC)O)C(=O)OC)OC(=O)C

Technology Process of 1H,7H-Naphtho(1,8-bc:4,4a-c')difuran-5,10a(8H)-dicarboxylic acid, 10-(acetyloxy)octahydro-3,5-dihydroxy-4-methyl-8-(((2E)-2-methyl-1-oxo-2-butenyl)oxy)-4-((1aR,2S,3aS,6aS,7S,7aS)-3a,6a,7,7a-tetrahydro-6a-hydroxy-7a-methyl-2,7-methanofuro(2,3-b)oxireno(e)oxepin-1a(2H)-yl)-, dimethyl ester, (2aR,3S,4S,4aR,5S,7aS,8R,10R,10aS,10bR)-

There total 6 articles about 1H,7H-Naphtho(1,8-bc:4,4a-c')difuran-5,10a(8H)-dicarboxylic acid, 10-(acetyloxy)octahydro-3,5-dihydroxy-4-methyl-8-(((2E)-2-methyl-1-oxo-2-butenyl)oxy)-4-((1aR,2S,3aS,6aS,7S,7aS)-3a,6a,7,7a-tetrahydro-6a-hydroxy-7a-methyl-2,7-methanofuro(2,3-b)oxireno(e)oxepin-1a(2H)-yl)-, dimethyl ester, (2aR,3S,4S,4aR,5S,7aS,8R,10R,10aS,10bR)- 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: 100.0%

23-α,β-acetoxy-22,23-dihydroazadirachtin (122437-48-3,125278-90-2,130932-04-6) → azadirachtin (11141-17-6,95507-03-2)

Guidance literature:

at 175 ℃; for 0.0833333h; under 0.002 Torr;

DOI:10.1016/S0040-4039(00)82888-9

Reference yield: 85.0%

C41H50O16Se → azadirachtin (11141-17-6,95507-03-2)

Guidance literature:

With pyridine; dihydrogen peroxide; In 1,2-dichloro-ethane; at 0 ℃; for 0.166667h;

DOI:10.1021/ol7027898

Reference yield: 67.0%

22,23-dihydro-23-β-thiophenoxyazadirachtin (167101-22-6) → azadirachtin (11141-17-6,95507-03-2)

Guidance literature:

22,23-dihydro-23-β-thiophenoxyazadirachtin; With 3,3-dimethyldioxirane; In dichloromethane; at -78 - 20 ℃;

In dichloromethane; toluene; Further stages.; Heating;

DOI:10.1002/anie.200703028

upstream raw materials:

23-α,β-acetoxy-22,23-dihydroazadirachtin

22,23-dihydro-23-β-thiophenoxyazadirachtin

Downstream raw materials:

dimethyl (2aR,4S,4aS,5S,7aS,8S,10R,10aR,10bR)-5-methoxy-4-methyl-3-oxo-8,10-phenylmethylenedioxy-4-phenylselenenoperhydronaphtho<1,8-bc:4,4a-c'>difuran-5,10a-dicarboxylate

dimethyl (2aR,4aS,5S,7aS,8S,10R,10aR,10bR)-5-methoxy-3-oxo-8,10-phenylmethylenedioxy-4-methylideneneperhydronaphtho<1,8-bc:4,4a-c'>difuran-5,10a-dicarboxylate

22,23-dihydro-23-α,β-isopropoxyazadirachtin

22,23-dihydro-23-β-isopropoxyazadirachtin

Refernces

• 1、 Ley, Steven V.,Abad-Somovilla, Antonio,Anderson, James C.,Ayats, Carles,Baenteli, Rolf,Beckmann, Edith,Boyer, Alistair,Brasca, Maria G.,Brice, Abigail,Broughton, Howard B.,Burke, Brenda J.,Cleator, Ed,Craig, Donald,Denholm, Alastair A.,Denton, Ross M.,Durand-Reville, Thomas,Gobbi, Luca B.,Goebel, Michael,Gray, Brian Lawrence,Grossmann, Robert B.,Gutteridge, Claire E.,Hahn, Norbert,Harding, Sarah L.,Jennens, David C.,Jennens, Lynn,Lovell, Peter J.,Lovell, Helen J.,De La Puente, Mary L.,Kolb, Hartmuth C.,Koot, Win-Jan,Maslen, Sarah L.,McCusker, Catherine F.,Mattes, Amos,Pape, Andrew R.,Pinto, Andrea,Santafianos, Dinos,Scott, James S.,Smith, Stephen C.,Somers, Andrew Q.,Spilling, Christopher D.,Stelzer, Frank,Toogood, Peter L.,Turner, Richard M.,Veitch, Gemma E.,Wood, Anthony,Zumbrunn, Cornelia. "The synthesis of azadirachtin: A potent insect antifeedant". experimental part. p. 10683 - 10704. Retrieved 2009/12/31.
• 2、 Denholm, Alastair A.,Jennens, Lyn,Ley, Steven V.,Wood, Anthony. "Chemistry of Insect Antifeedants from Azadirachta Indica (Part 19): A Potential Relay Route for the Synthesis of Azadirachtin.". . p. 6591 - 6604. Retrieved 2007/10/02.