ethyl 13-cis-retinoate

Base Information

• Chemical Name: ethyl 13-cis-retinoate
• CAS No.: 59699-82-0
• Molecular Formula: C₂₂H₃₂O₂
• Molecular Weight: 328.495
• Mol file: 59699-82-0.mol

Synonyms:ethyl 13-cis-retinoate

Chemical Property of ethyl 13-cis-retinoate

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of ethyl 13-cis-retinoate

There total 37 articles about ethyl 13-cis-retinoate 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: 60.0%

ethanol (64-17-5) + 13-cis-vitamin A aldehyde (472-86-6) → ethyl 13-cis-retinoate (59699-82-0,24519-09-3)

Guidance literature:

With manganese(IV) oxide; silver(II) oxide; sodium cyanide; at 40 ℃; for 14h;

DOI:10.1021/jo00272a032

Reference yield: 58.0%

ethanol (64-17-5) + retinol (68-26-8,2052-63-3,6018-74-2,17706-49-9,22737-96-8,22737-97-9,29444-25-5,34218-73-0,39815-04-8,69686-68-6,69686-69-7,74743-94-5,84415-27-0,84415-28-1,85354-09-2,85354-10-5,93380-02-0,98462-62-5,137121-52-9) → ethyl retinoate (3899-20-5,51249-34-4,59699-82-0,85354-08-1,86708-67-0,86708-68-1,86708-69-2,86708-70-5,24519-09-3)

Guidance literature:

With manganese(IV) oxide; sodium cyanide; In acetic acid; acetonitrile; at 20 ℃; for 62h;

DOI:10.1021/jm00081a020

Reference yield: 43.0%

(3E,5E)-4-methyl-6-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3,5-hexadien-1-yne (25576-25-4) + ethyl (Z)-3-(((trifluoromethyl)sulfonyl)oxy)but-2-enoate (122135-84-6) → ethyl 13-cis-retinoate (59699-82-0,24519-09-3)

Guidance literature:

(3E,5E)-4-methyl-6-(2,6,6-trimethyl-1-cyclohexen-1-yl)-3,5-hexadien-1-yne; With nBu₃Sn(nBu)Cu(CN)Li₂; In tetrahydrofuran; at -78 ℃;

ethyl (Z)-3-(((trifluoromethyl)sulfonyl)oxy)but-2-enoate; With triphenyl-arsane; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1055/s-2001-14908

upstream raw materials:

(2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal

triethyl 3-methyl-4-phosphonocrotonate

(2E,4E,6E)-8-Acetoxy-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6-trienoic acid ethyl ester

ethanol

Downstream raw materials:

all-trans-retinoic-acid

7-cis-retinoic acid

ethyl (all-E)-retinoate

9,11,13-tri-cis-ethyl retinoate

Refernces

• 1、 Tanaka,Kagechika,Kawachi,Fukasawa,Hashimoto,Shudo. "Base-catalyzed isomerization of retinoic acid. Synthesis and differentiation-inducing activities of 14-alkylated all-trans-, 13-cis-, and 20,14-retro-retinoic acids". . p. 567 - 572. Retrieved 2007/10/02.
• 2、 Solladie,Girardin,Metra. "Highly stereoselective synthesis of 13-cis retinoic acid by low-valent titanium induced reductive elimination". . p. 209 - 212. Retrieved 2007/10/02.