3-Penten-2-ol, acetate, (2R,3E)-

Base Information

• Chemical Name: 3-Penten-2-ol, acetate, (2R,3E)-
• CAS No.: 19248-95-4
• Molecular Formula: C7H12O2
• Molecular Weight: 128.171
• Mol file: 19248-95-4.mol

Synonyms:

Chemical Property of 3-Penten-2-ol, acetate, (2R,3E)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-Penten-2-ol, acetate, (2R,3E)-

There total 5 articles about 3-Penten-2-ol, acetate, (2R,3E)- 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: 45.0%

vinyl acetate (108-05-4,9003-20-7) + 3-penten-2-ol (1569-50-2) → (2S,3E)-pent-3-en-2-ol (1569-50-2,3899-34-1,24652-50-4,31001-81-7,35666-69-4,42569-15-3,42569-16-4,60102-79-6,60102-80-9,79646-46-1,95782-14-2,926-58-9) + (R,E)-pent-3-en-2-yl acetate (19248-95-4)

Guidance literature:

With Novozyme 435 (lipase acrylic resin from Candida antarctica); In pentane; at 20 ℃; for 3h; optical yield given as %ee; Molecular sieve; Enzymatic reaction;

DOI:10.1021/ja304872j

Reference yield: 38.0%

vinyl acetate (108-05-4,9003-20-7) + 3-penten-2-ol (1569-50-2) + (S)-3-tert-butoxycarbonylamino-4-phenylbutanoic acid (51871-62-6) → (S,E)-pent-3-en-2-yl (S)-3-(tert-butoxycarbonylamino)-4-phenylbutanoate (1401088-84-3) + (R,E)-pent-3-en-2-yl acetate (19248-95-4)

Guidance literature:

vinyl acetate; 3-penten-2-ol; at 20 ℃; for 24h; Enzymatic reaction;

(S)-3-tert-butoxycarbonylamino-4-phenylbutanoic acid; With dmap; dicyclohexyl-carbodiimide; In diethyl ether; at 0 - 20 ℃; stereoselective reaction;

DOI:10.1021/jo301693d

Reference yield: 18.0%

(furan-2-yloxy)-trimethylsilane (61550-02-5) + 3-penten-2-yl acetate (31001-80-6) → C9H12O2 + (-)-(R)-(E)-3-(pent-3-en-2-yl)furan-2(5H)-one (1380438-82-3) + (+)-(S)-(E)-3-(pent-3-en-2-yl)furan-2(5H)-one + (-)-(S)-(E)-pent-3-en-2-yl acetate (10500-12-6,19248-95-4,19248-96-5,29393-13-3,31001-80-6,146566-17-8,148553-12-2,150849-57-3,131616-47-2)

Guidance literature:

(furan-2-yloxy)-trimethylsilane; With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; (1R,2R)-1,2-bis[(2-diphenylphosphanyl)benzoylamino]cyclohexane; In dichloromethane; at 20 ℃; for 0.25h; Inert atmosphere;

3-penten-2-yl acetate; In dichloromethane; at 0 ℃; for 0.5h; optical yield given as %ee; enantioselective reaction; Inert atmosphere; Resolution of racemate;

DOI:10.1002/anie.201109075

upstream raw materials:

thiobenzoic acid potassium salt

3-penten-2-yl acetate

(furan-2-yloxy)-trimethylsilane

vinyl acetate

Downstream raw materials:

diethyl 1-methyl-2-butenylmalonate

C₁₂H₁₇N

Benzyl-((E)-(S)-1-methyl-but-2-enyl)-amine

Refernces

• 1、 Mao, Bin,Ji, Yining,Fananas-Mastral, Martin,Caroli, Giuseppe,Meetsma, Auke,Feringa, Ben L.. "Highly enantioselective synthesis of 3-substituted furanones by palladium-catalyzed kinetic resolution of unsymmetrical allyl acetates". supporting information; experimental part. p. 3168 - 3173. Retrieved 2012/05/05.
• 2、 Luessem, Bernhard J.,Gais, Hans-Joachim. "Palladium-catalyzed enantioselective allylic alkylation of thiocarboxylate ions: Asymmetri synthesis of allylic thioesters and memory effect/dynamic kinetic resolution of allylic esters". . p. 4041 - 4052. Retrieved 2007/10/03.