(4S)-ethyl 4-phenyl-2-hydroxy-5-oxo-2,3,4,5-tetrahydropyrano-[3,2-c]chromene-2-carboxylate

Base Information

• Chemical Name: (4S)-ethyl 4-phenyl-2-hydroxy-5-oxo-2,3,4,5-tetrahydropyrano-[3,2-c]chromene-2-carboxylate
• CAS No.: 1314033-57-2
• Molecular Formula: C₂₁H₁₈O₆
• Molecular Weight: 366.37
• Mol file: 1314033-57-2.mol

Synonyms:(4S)-ethyl 4-phenyl-2-hydroxy-5-oxo-2,3,4,5-tetrahydropyrano-[3,2-c]chromene-2-carboxylate

Chemical Property of (4S)-ethyl 4-phenyl-2-hydroxy-5-oxo-2,3,4,5-tetrahydropyrano-[3,2-c]chromene-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S)-ethyl 4-phenyl-2-hydroxy-5-oxo-2,3,4,5-tetrahydropyrano-[3,2-c]chromene-2-carboxylate

There total 4 articles about (4S)-ethyl 4-phenyl-2-hydroxy-5-oxo-2,3,4,5-tetrahydropyrano-[3,2-c]chromene-2-carboxylate 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: 95.0%

4-hydroxy[1]benzopyran-2-one (1076-38-6,92395-12-5) + (E)-ethyl-2-oxo-4-phenylbut-3-enoate (17451-20-6,55674-14-1,55629-96-4) → (4S)-ethyl 4-phenyl-2-hydroxy-5-oxo-2,3,4,5-tetrahydropyrano-[3,2-c]chromene-2-carboxylate (1314033-57-2)

Guidance literature:

With C₃₄H₃₇F₃N₆O₄; In dichloromethane; at 20 ℃; for 1.5h; enantioselective reaction;

DOI:10.1021/acs.joc.8b01847

Reference yield:

4-hydroxy[1]benzopyran-2-one (1076-38-6,92395-12-5) + ethyl 4-phenyl-2-oxobut-3-enoate (55629-96-4,55674-14-1,17451-20-6) → (4R)-ethyl 4-phenyl-2-hydroxy-5-oxo-2,3,4,5-tetrahydropyrano-[3,2-c]chromene-2-carboxylate (1228363-08-3) + (4S)-ethyl 4-phenyl-2-hydroxy-5-oxo-2,3,4,5-tetrahydropyrano-[3,2-c]chromene-2-carboxylate (1314033-57-2)

Guidance literature:

With bis(acetylacetonate)nickel(II); C₃₅H₅₂N₄O₄; In 1,2-dichloro-ethane; at 0 - 20 ℃; for 9h; optical yield given as %ee; enantioselective reaction; Molecular sieve;

DOI:10.1016/j.tetlet.2011.04.089

Reference yield:

3H-chromene-2,4-dione (4438-85-1) + ethyl 4-phenyl-2-oxobut-3-enoate (55629-96-4,55674-14-1,17451-20-6) → (4R)-ethyl 4-phenyl-2-hydroxy-5-oxo-2,3,4,5-tetrahydropyrano-[3,2-c]chromene-2-carboxylate (1228363-08-3) + (4S)-ethyl 4-phenyl-2-hydroxy-5-oxo-2,3,4,5-tetrahydropyrano-[3,2-c]chromene-2-carboxylate (1314033-57-2)

Guidance literature:

With C₆₈H₉₀N₆O₈; In dichloromethane; at 25 ℃; Overall yield = 77 percent; Optical yield = 90 percent ee;

upstream raw materials:

4-hydroxy[1]benzopyran-2-one

(E)-ethyl-2-oxo-4-phenylbut-3-enoate

ethyl 4-phenyl-2-oxobut-3-enoate

3H-chromene-2,4-dione