6-Heptenoic acid, 5-hydroxy-3-oxo-7-phenyl-, ethyl ester, (5R,6E)-

Base Information

• Chemical Name: 6-Heptenoic acid, 5-hydroxy-3-oxo-7-phenyl-, ethyl ester, (5R,6E)-
• CAS No.: 735287-46-4
• Molecular Formula: C15H18O4
• Molecular Weight: 262.306
• Mol file: 735287-46-4.mol

Synonyms:

Chemical Property of 6-Heptenoic acid, 5-hydroxy-3-oxo-7-phenyl-, ethyl ester, (5R,6E)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 6-Heptenoic acid, 5-hydroxy-3-oxo-7-phenyl-, ethyl ester, (5R,6E)-

There total 12 articles about 6-Heptenoic acid, 5-hydroxy-3-oxo-7-phenyl-, ethyl ester, (5R,6E)- 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: 88.0%

ethyl potassium malonate (6148-64-7) + (E,R)-3-hydroxy-1-((S)-4-isopropyl-2-thioxothiazolidin-3-yl)-5-phenylpent-4-en-1-one (101979-49-1) → ethyl (E,R)-5-hydroxy-3-oxo-7-phenylhept-6-enoate (735287-46-4)

Guidance literature:

With 1H-imidazole; magnesium chloride; In ethanol; at 20 ℃; for 7h;

DOI:10.1021/ol0493960

Reference yield: 85.0%

(E)-3-phenylpropenal (14371-10-9) + 1-ethoxy-1,3-bis[(trimethylsilyl)oxy]buta-1,3-diene (89186-81-2) → ethyl (E,R)-5-hydroxy-3-oxo-7-phenylhept-6-enoate (735287-46-4)

Guidance literature:

(E)-3-phenylpropenal; 1-ethoxy-1,3-bis[(trimethylsilyl)oxy]buta-1,3-diene; With titanium(IV) isopropylate; (R)-1,1'-Bi-2-naphthol; In tetrahydrofuran; at -78 - 20 ℃; Molecular sieve; Inert atmosphere;

With trifluoroacetic acid; In tetrahydrofuran; at -78 - 20 ℃; optical yield given as %ee; enantioselective reaction; Inert atmosphere;

DOI:10.1016/j.tetlet.2010.12.070

Reference yield: 85.0%

5-(tert-butyl-dimethyl-silanyloxy)-3-oxo-7-phenyl-hept-6-enoic acid ethyl ester (917251-14-0) → ethyl (E,R)-5-hydroxy-3-oxo-7-phenylhept-6-enoate (735287-46-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 2h;

DOI:10.1016/j.tetlet.2006.09.122

upstream raw materials:

ethyl potassium malonate

(E,R)-3-hydroxy-1-((S)-4-isopropyl-2-thioxothiazolidin-3-yl)-5-phenylpent-4-en-1-one

5-(tert-butyl-dimethyl-silanyloxy)-3-oxo-7-phenyl-hept-6-enoic acid ethyl ester

(3R,4E)-3-(tert-butyldimethylsilanyloxy)-5-phenylpent-4-enal

Downstream raw materials:

C₁₅H₂₀O₄

ethyl 2-((4R,6R)-2,2-dimethyl-6-((E)-styryl)-1,3-dioxan-4-yl)acetate

2-((4R,6R)-2,2-dimethyl-6-((E)-styryl)-1,3-dioxan-4-yl)acetaldehyde

C₂₀H₂₆O₄

Refernces

• 1、 Kumar, Rayala Naveen,Meshram. "Total synthesis of (-)-diospongin A and (+)-cryptofolione via asymmetric aldol reaction". experimental part. p. 1003 - 1007. Retrieved 2011/03/21.
• 2、 Sabitha, Gowravaram,Sudhakar,Yadav. "Application of the Cosford cross-coupling protocol for the stereoselective synthesis of (R)-(+)-goniothalamin, (R)-(+)-kavain and (S)-(+)-7,8-dihydrokavain". . p. 8599 - 8602. Retrieved 2007/10/03.