(4S,5S,6E,8S,9E,14R)-5,8-dihydroxy-14-methyl-4-phenylthiooxacyclotetradeca-6,9-dien-2-one

Base Information

• Chemical Name: (4S,5S,6E,8S,9E,14R)-5,8-dihydroxy-14-methyl-4-phenylthiooxacyclotetradeca-6,9-dien-2-one
• CAS No.: 277317-10-9
• Molecular Formula: C₂₀H₂₆O₄S
• Molecular Weight: 362.49
• Mol file: 277317-10-9.mol

Synonyms:(4S,5S,6E,8S,9E,14R)-5,8-dihydroxy-14-methyl-4-phenylthiooxacyclotetradeca-6,9-dien-2-one

Chemical Property of (4S,5S,6E,8S,9E,14R)-5,8-dihydroxy-14-methyl-4-phenylthiooxacyclotetradeca-6,9-dien-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S,6E,8S,9E,14R)-5,8-dihydroxy-14-methyl-4-phenylthiooxacyclotetradeca-6,9-dien-2-one

There total 1 articles about (4S,5S,6E,8S,9E,14R)-5,8-dihydroxy-14-methyl-4-phenylthiooxacyclotetradeca-6,9-dien-2-one 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: 73.0%

thiophenol (108-98-5) + palmarumycin C13 (152607-03-9) → (4S,5S,6E,8S,9E,14R)-5,8-dihydroxy-14-methyl-4-phenylthiooxacyclotetradeca-6,9-dien-2-one (277317-10-9) + (4R,5S,6E,8S,9E,14R)-5,8-dihydroxy-14-methyl-4-phenylthiooxacyclotetradeca-6,9-dien-2-one

Guidance literature:

With triethylamine; In acetone; at -78 - 20 ℃;

DOI:10.1002/(SICI)1099-0690(200004)2000:8<1451::AID-EJOC1451>3.0.CO;2-F

Reference yield:

(S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride (39637-99-5,20445-33-4) + (4S,5S,6E,8S,9E,14R)-5,8-dihydroxy-14-methyl-4-phenylthiooxacyclotetradeca-6,9-dien-2-one (277317-10-9) → (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (6E,9E)-(4S,5S,8S,14R)-14-methyl-2-oxo-4-phenylsulfanyl-8-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-oxacyclotetradeca-6,9-dien-5-yl ester

Guidance literature:

With pyridine; dmap; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1002/(SICI)1099-0690(200004)2000:8<1451::AID-EJOC1451>3.0.CO;2-F

Reference yield:

(R)-methoxytrifluoromethylphenylacetyl chloride (20445-33-4,39637-99-5) + (4S,5S,6E,8S,9E,14R)-5,8-dihydroxy-14-methyl-4-phenylthiooxacyclotetradeca-6,9-dien-2-one (277317-10-9) → (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (6E,9E)-(4S,5S,8S,14R)-14-methyl-2-oxo-4-phenylsulfanyl-8-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-oxacyclotetradeca-6,9-dien-5-yl ester

Guidance literature:

With pyridine; dmap; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1002/(SICI)1099-0690(200004)2000:8<1451::AID-EJOC1451>3.0.CO;2-F

upstream raw materials:

thiophenol

palmarumycin C₁₃