aspicilin

Base Information

• Chemical Name: aspicilin
• CAS No.: 52461-05-9
• Molecular Formula: C18H32O5
• Molecular Weight: 328.44
• Mol file: 52461-05-9.mol

Synonyms:(2E,4R,5S,6R,17S)-4,5,6-trihydroxyoctadeca-2-en-17-olid;(+)-Aspicilin;(E)-(5R,6S,7R,18S)-5,6,7-Trihydroxy-18-methyl-oxacyclooctadec-3-en-2-one;

Chemical Property of aspicilin

Chemical Property:

• Melting Point: 151 - 152 °C
• Boiling Point: 512.1±50.0 °C(Predicted)
• PKA: 13.10±0.70(Predicted)
• PSA: 86.99000
• Density: 1.055±0.06 g/cm3(Predicted)
• LogP: 2.47160

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of aspicilin

There total 142 articles about aspicilin 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: 91.0%

(1R,2E,6S,17R,18S)-17-Hydroxy-6,20,20-trimethyl-5,19,21-trioxabicyclo<16.3.0>henicos-2-en-4-on (99096-82-9) → (+)-aspicilin (52461-05-9)

Guidance literature:

With trifluoroacetic acid; In methanol; water; at 70 ℃; for 3h;

DOI:10.1021/acs.joc.7b01702

Reference yield: 86.0%

C27H50O5Si (1374433-47-2) → (+)-aspicilin (52461-05-9)

Guidance literature:

With hydrogenchloride; In methanol; at 0 ℃; for 5h;

DOI:10.1002/ejoc.201101673

Reference yield: 86.0%

C38H58O5Si (1202569-76-3) → (+)-aspicilin (52461-05-9)

Guidance literature:

With titanium tetrachloride; In dichloromethane; at 0 - 20 ℃;

DOI:10.1055/s-0029-1217974

upstream raw materials:

(2E,4R,5S,6R,17S)-4,5-(Carbonyldioxy)-6-hydroxyoctadec-2-en-17-olid

(3E,5Z,7R,18S)-7-hydroxy-18-methyloxacyclooctadeca-3,5-dien-2-one

(2E,4S,5S,6R,17S)-4,5-Epoxy-6-hydroxyoctadec-2-en-17-olid

(1R,2E,6S,17R,18S)-17-<(2-Methoxyethoxy)methoxy>-6,20,20-trimethyl-5,19,21-trioxabicyclo<16.3.0>henicos-2-en-4-on

Refernces

• 1、 Oppolzer, Wolfgang,Radinov, Rumen N.,Brabander, Jef De. "Total Synthesis of the Macrolide (+)-Aspicilin by an Asymmetrically Catalyzed Macrocyclization of an ω-Alkynal Ester". . p. 2607 - 2610. Retrieved 1995.
• 2、 Dixon, Darren J.,Foster, Alison C.,Ley, Steven V.. "A short and efficient stereoselective synthesis of the polyhydroxylated macrolactone (+)-aspicilin". . p. 123 - 125. Retrieved 2000.
• 3、 Schmidt, René,Ostermeier, Michael,Schobert, Rainer. "Wittig Cyclization of ω-Hydroxy Hemiacetals: Synthesis of (+)-Aspicilin". . p. 9126 - 9132. Retrieved 2017/09/11.
• 4、 Raji Reddy, Chada,Rao, Nagavaram Narsimha,Sujitha, Pombala,Kumar, Chityal Ganesh. "Total synthesis of (+)-aspicilin by an alkyne-based approach and its biological evaluation". . p. 1819 - 1824. Retrieved 2012/05/20.