Azuleno[4,5-b]furan-2(3H)-one, decahydro-4,8-dihydroxy-3,6,9-tris(methylene)-

Base Information

• Chemical Name: Azuleno[4,5-b]furan-2(3H)-one, decahydro-4,8-dihydroxy-3,6,9-tris(methylene)-
• CAS No.: 35932-46-8
• Molecular Formula: C₁₅H₁₈O₄
• Molecular Weight: 262.306
• Mol file: 35932-46-8.mol

Synonyms:

Chemical Property of Azuleno[4,5-b]furan-2(3H)-one, decahydro-4,8-dihydroxy-3,6,9-tris(methylene)-

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 Azuleno[4,5-b]furan-2(3H)-one, decahydro-4,8-dihydroxy-3,6,9-tris(methylene)-

There total 17 articles about Azuleno[4,5-b]furan-2(3H)-one, decahydro-4,8-dihydroxy-3,6,9-tris(methylene)- 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: 75.0%

(3aR,4S,6aR,8S,9aR,9bR)-8-((tert-butyldimethylsilyl)oxy)-4-hydroxy-3,6,9-trimethylenedecahydroazuleno[4,5-b]furan-2(9bH)-one → deacylcynaropicrin (35932-46-8,89647-87-0,31565-50-1,35730-79-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃; for 6h; Inert atmosphere;

DOI:10.1016/j.bmcl.2019.04.004

Reference yield: 68.0%

(1R,3S,5R,6R,7R,8S)-8-hydroxy-3-(methoxymethoxy)-13,14,15-trimethylenedecahydroazuleno[6,7-β]furan-12-one (1549718-88-8) → deacylcynaropicrin (35932-46-8,89647-87-0,31565-50-1,35730-79-1)

Guidance literature:

With pyridinium p-toluenesulfonate; In tert-butyl alcohol; for 28h; Inert atmosphere; Reflux;

DOI:10.1016/j.bmcl.2013.12.099

Reference yield: 60.0%

cynaporicrin (35932-39-9,35730-78-0) → 11,13-dihydro-13-hydroxydeacylcynaropicrin + deacylcynaropicrin (35932-46-8,89647-87-0,31565-50-1,35730-79-1)

Guidance literature:

With potassium carbonate; at 50 ℃; for 24h;

DOI:10.1016/j.tet.2006.05.058

upstream raw materials:

8-epideacylcynaropicrin-3-O-β-D-glucopyranoside

ixerin M

ixerin N

ixerin R

Downstream raw materials:

pulchellamine A

pulchellamine D

8α-acetoxyzaluzanin D

Refernces

• 1、 Samek,Holub. "". . p. 4775. Retrieved 1971.
• 2、 Usuki, Toyonobu,Sato, Makiko,Hara, Shihori,Yoshimoto, Yukiko,Kondo, Ryosuke,Zimmermann, Stefanie,Kaiser, Marcel,Brun, Reto,Hamburger, Matthias,Adams, Michael. "Antitrypanosomal structure-activity-relationship study of synthetic cynaropicrin derivatives". . p. 794 - 798. Retrieved 2014/02/14.
• 3、 Nishimura,Miyase,Ueno,et al.. "Sesquiterpene lactones from Ixeris stolonifera A. GRAY". . p. 3361 - 3368. Retrieved 2007/10/02.