(-)-juvenile hormone I

Base Information

• Chemical Name: (-)-juvenile hormone I
• CAS No.: 33212-31-6
• Molecular Formula: C₁₈H₃₀O₃
• Molecular Weight: 294.434
• Mol file: 33212-31-6.mol

Synonyms:(-)-juvenile hormone I

Chemical Property of (-)-juvenile hormone I

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-juvenile hormone I

There total 46 articles about (-)-juvenile hormone I 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: 79.0%

(2E,6E)-(10S,11S)-7-Ethyl-11-hydroxy-10-methanesulfonyloxy-3,11-dimethyl-trideca-2,6-dienoic acid methyl ester (119615-14-4) → methyl (2E,6E,10R,11S)-10,11-epoxy-7-ethyl-3,11-dimethyl-2,6-tridecanoate (17793-96-3,17941-67-2,17941-68-3,17941-69-4,17941-70-7,22329-85-7,22329-86-8,22329-87-9,22395-76-2,23314-84-3,23314-95-6,23314-97-8,23314-99-0,25506-76-7,25506-77-8,25506-78-9,25506-79-0,25506-80-3,25506-81-4,33212-31-6,33262-11-2,33262-12-3,84847-83-6,84847-84-7,84847-85-8,13804-51-8)

Guidance literature:

With sodium methylate; In methanol; at 0 ℃; for 0.166667h;

DOI:10.1016/S0040-4020(01)85826-9

Reference yield: 79.0%

C24H34O6S (1389395-08-7) + dimethyl zinc(II) (544-97-8) → methyl (2E,6E,10R,11S)-10,11-epoxy-7-ethyl-3,11-dimethyl-2,6-tridecanoate (17793-96-3,17941-67-2,17941-68-3,17941-69-4,17941-70-7,22329-85-7,22329-86-8,22329-87-9,22395-76-2,23314-84-3,23314-95-6,23314-97-8,23314-99-0,25506-76-7,25506-77-8,25506-78-9,25506-79-0,25506-80-3,25506-81-4,33212-31-6,33262-11-2,33262-12-3,84847-83-6,84847-84-7,84847-85-8,13804-51-8)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1055/s-0031-1290803

Reference yield:

(2E,6E)-(10S,11R)-7-Ethyl-11-hydroxy-10-methanesulfonyloxy-3,11-dimethyl-trideca-2,6-dienoic acid methyl ester → methyl (2E,6E,10R,11S)-10,11-epoxy-7-ethyl-3,11-dimethyl-2,6-tridecanoate (17793-96-3,17941-67-2,17941-68-3,17941-69-4,17941-70-7,22329-85-7,22329-86-8,22329-87-9,22395-76-2,23314-84-3,23314-95-6,23314-97-8,23314-99-0,25506-76-7,25506-77-8,25506-78-9,25506-79-0,25506-80-3,25506-81-4,33212-31-6,33262-11-2,33262-12-3,84847-83-6,84847-84-7,84847-85-8,13804-51-8)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 0.5h;

DOI:10.1002/1099-0690(200106)2001:11<2145::AID-EJOC2145>3.0.CO;2-J

upstream raw materials:

(2E,6E)-7-Ethyl-9-((2R,3S)-3-ethyl-3-methyl-oxiranyl)-3-methyl-nona-2,6-dienoic acid methyl ester

(2E,6E)-(10S,11S)-7-Ethyl-11-hydroxy-10-methanesulfonyloxy-3,11-dimethyl-trideca-2,6-dienoic acid methyl ester

methyl (2E,6E,10E)-7-ethyl-3,11-dimethyltrideca-2,6,10-trienone

(3E)-1-iodo-4-methylhex-3-ene

Downstream raw materials:

methyl (2E,6E,10R,11S)-10,11-epoxy-7-ethyl-3,11-dimethyl-2,6-tridecanoate

Refernces

• 1、 Okochi,Mori. "New enantioselective synthesis of (10R, 11S)-(+)-juvenile hormones I and II". . p. 2145 - 2150. Retrieved 2007/10/03.
• 2、 Peter, Martin G.,Stupp, Hans-Peter,Lentes, Klaus-Ulrich. "Umkehr der Enantioselektivitaet bei der enzymatischen Hydrolyse von Juvenilhormon als Ergebnis einer Proteinfraktionierung". . p. 794 - 795. Retrieved 2007/10/02.