Cryptofolione

Base Information

• Chemical Name: Cryptofolione
• CAS No.: 160098-78-2
• Molecular Formula: C19H22 O4
• Molecular Weight: 314.38
• Mol file: 160098-78-2.mol

Synonyms:2H-Pyran-2-one,6-(4,6-dihydroxy-8-phenyl-1,7-octadienyl)-5,6-dihydro-,[6R-[6R*(1E,4S*,6R*,7E)]]-; 2H-Pyran-2-one,6-[(1E,4S,6R,7E)-4,6-dihydroxy-8-phenyl-1,7-octadienyl]-5,6-dihydro-, (6R)-(9CI); (6R,10S,12R)-Cryptomoscatone E2; Cryptofolione; Cryptomoscatone E2

Chemical Property of Cryptofolione

Chemical Property:

• PSA: 66.76000
• LogP: 2.62970

Purity/Quality:

98%Min ^*data from raw suppliers

Cryptofolione 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Cryptofolione

There total 35 articles about Cryptofolione 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: 93.0%

(6R)-6-((1E)-3-{(4S,6R)-2,2-dimethyl-6-[(E)-2-phenylvinyl]-1,3-dioxan-4-yl}prop-1-en-1-yl)-5,6-dihydro-2H-pyran-2-one → (6R)-5,6-dihydro-6-[(4'S*,6'R*,1'E,7'E)-4',6'-dihydroxy-8'-phenyl-1',7'-octadienyl]-2-pyrone (160098-78-2)

Guidance literature:

With hydrogenchloride; water; In acetonitrile; at 0 ℃; for 0.5h; Inert atmosphere;

DOI:10.1055/s-0030-1258215

Reference yield: 91.0%

cryptofolione acetonide → (6R)-5,6-dihydro-6-[(4'S*,6'R*,1'E,7'E)-4',6'-dihydroxy-8'-phenyl-1',7'-octadienyl]-2-pyrone (160098-78-2)

Guidance literature:

With camphor-10-sulfonic acid; In methanol; at 20 ℃; for 2h;

DOI:10.1016/j.tetlet.2010.12.070

Reference yield: 83.0%

(R)-6-[(1E,4S,6R,7E)-4,6-bis{[tert-butyl(dimethyl)silyl]oxy}-8-phenylocta-1,7-dien-1-yl]-5,6-dihydro-2H-pyran-2-one (678970-59-7) → (6R)-5,6-dihydro-6-[(4'S*,6'R*,1'E,7'E)-4',6'-dihydroxy-8'-phenyl-1',7'-octadienyl]-2-pyrone (160098-78-2)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; water; at 0 - 20 ℃; for 3h;

DOI:10.1055/s-0031-1290771

upstream raw materials:

(R)-6-[(1E,4S,6R,7E)-4,6-bis{[tert-butyl(dimethyl)silyl]oxy}-8-phenylocta-1,7-dien-1-yl]-5,6-dihydro-2H-pyran-2-one

(4R,6R)-6-((E)-Styryl)-tetrahydro-pyran-2,4-diol

(2S,4R,6R)-2-Methoxy-6-((E)-styryl)-tetrahydro-pyran-4-ol

(2S,6R)-2-Methoxy-6-((E)-styryl)-tetrahydro-pyran-4-one

Refernces

• 1、 Balasubramanyam,Chinna Reddy, Gandolla,Salvanna, Nayaki,Das, Biswanath. "Efficient stereoselective total synthesis of (+)-cryptofolione and the first synthesis of (-)-cryptocaryalactone". experimental part. p. 3706 - 3710. Retrieved 2011/12/16.
• 2、 Sabitha, Gowravaram,Reddy, S. Siva Sankara,Reddy, D. Vasudeva,Bhaskar, Vangala,Yadav, Jhillu S.. "Stereoselective approaches to the total synthesis of (6R,4′S, 6′R)-cryptofolione". experimental part. p. 3453 - 3460. Retrieved 2010/11/20.