(+)-Methoprene;(7S)-Methoprene;ZR 2458

Base Information

• Chemical Name: (+)-Methoprene;(7S)-Methoprene;ZR 2458
• CAS No.: 52020-07-2
• Molecular Formula: C₁₉H₃₄O₃
• Molecular Weight: 310.477
• DSSTox Substance ID: DTXSID70860572
• Mol file: 52020-07-2.mol

Synonyms:Altosid;Altosid PS 10;Altosid PS-10;Altosid PS10;Methoprene;ZR 515;ZR-515;ZR515

Chemical Property of (+)-Methoprene;(7S)-Methoprene;ZR 2458

Chemical Property:

• XLogP3: 5.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 11
• Exact Mass: 310.25079494
• Heavy Atom Count: 22
• Complexity: 378

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)OC(=O)C=C(C)C=CCC(C)CCCC(C)(C)OC

Technology Process of (+)-Methoprene;(7S)-Methoprene;ZR 2458

There total 9 articles about (+)-Methoprene;(7S)-Methoprene;ZR 2458 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:

diisopropyl ester of 2-methyl-3-isopropoxycarbonyl-2-propenylphosphonic acid (50798-35-1) + S-(-)-7-methoxy-3,7-dimethyloctanal (134678-53-8) → 2-cis-4-trans-S-methoprene (134678-54-9) + (2Z,4E)-(R)-11-Methoxy-3,7,11-trimethyl-dodeca-2,4-dienoic acid isopropyl ester (36557-27-4,40596-69-8,41205-06-5,52020-07-2,52341-11-4,53108-97-7,65733-16-6,65733-17-7,134678-54-9) + R-(-)-11-methoxy-3,7,11-trimethyl-2E,4E-dodecadienoic acid isopropyl ester (65733-17-7) + (S)-methoprene (65733-16-6)

Guidance literature:

With potassium hydroxide; In toluene; at 18 - 22 ℃; for 3h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1007/BF00958564

Reference yield:

3,7-dimethyl-oct-6-enal (106-23-0,26489-02-1) → S-(+)-11-methoxy-3,7,11-trimethyldodecadienoic acid isopropyl ester (36557-27-4,40596-69-8,41205-06-5,52020-07-2,52341-11-4,53108-97-7,65733-16-6,65733-17-7,134678-54-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 79 percent / diethyl ether / 15 h / 20 °C

2: O₂ / PdCl₂, CuCl / dimethylformamide; H₂O / 1 h

3: TsOH, Na₂SO₄ / benzene / 1 h / Heating

4: 80 percent / diethyl ether / 1.) -10 deg C, 3 h, 2.) warm to 20 deg C, 1 h

5: 1.) Hg(OAc)2, 2.) NaBH₄, NaOH / 1.) 5 deg C, 1 h; 20 deg C, 24 h, 2.) H₂O, 0 deg C

With sodium hydroxide; sodium tetrahydroborate; mercury(II) diacetate; oxygen; toluene-4-sulfonic acid; sodium sulfate; copper(l) chloride; palladium dichloride; In diethyl ether; water; N,N-dimethyl-formamide; benzene;

DOI:10.1007/BF00699984

Reference yield:

6,10-dimethylundeca-1,9-dien-4-ol (90660-54-1) → S-(+)-11-methoxy-3,7,11-trimethyldodecadienoic acid isopropyl ester (36557-27-4,40596-69-8,41205-06-5,52020-07-2,52341-11-4,53108-97-7,65733-16-6,65733-17-7,134678-54-9)

Guidance literature:

Multi-step reaction with 4 steps

1: O₂ / PdCl₂, CuCl / dimethylformamide; H₂O / 1 h

2: TsOH, Na₂SO₄ / benzene / 1 h / Heating

3: 80 percent / diethyl ether / 1.) -10 deg C, 3 h, 2.) warm to 20 deg C, 1 h

4: 1.) Hg(OAc)2, 2.) NaBH₄, NaOH / 1.) 5 deg C, 1 h; 20 deg C, 24 h, 2.) H₂O, 0 deg C

With sodium hydroxide; sodium tetrahydroborate; mercury(II) diacetate; oxygen; toluene-4-sulfonic acid; sodium sulfate; copper(l) chloride; palladium dichloride; In diethyl ether; water; N,N-dimethyl-formamide; benzene;

DOI:10.1007/BF00699984

upstream raw materials:

methanol

isopropyl 3,7,11-trimethyl-2ξ,4E,10-dodecatrienoate

3,7-dimethyl-oct-6-enal

6,10-dimethylundeca-1,9-dien-4-ol

Refernces

• 1、 Serebryakov, E. P.,Zhdankina, G. M.,Kryshtal', G. V.,Mavrov, M. V.,Khao, Nguen Kong. "TERPENES IN ORGANIC SYNTHESIS. 13. SYNTHESIS OF S-(+)-METHOPRENE FROM (+)-&β-CITRONELLENE". . p. 739 - 743. Retrieved 2007/10/02.