(7E,13E)-(4R,9R,10S,16S)-9-Benzyloxy-4,10,16-trimethyl-1,5,11-trioxa-cyclohexadeca-7,13-diene-2,6,12-trione

Base Information

• Chemical Name: (7E,13E)-(4R,9R,10S,16S)-9-Benzyloxy-4,10,16-trimethyl-1,5,11-trioxa-cyclohexadeca-7,13-diene-2,6,12-trione
• CAS No.: 455934-75-5
• Molecular Formula: C₂₃H₂₈O₇
• Molecular Weight: 416.471
• Mol file: 455934-75-5.mol

Synonyms:(7E,13E)-(4R,9R,10S,16S)-9-Benzyloxy-4,10,16-trimethyl-1,5,11-trioxa-cyclohexadeca-7,13-diene-2,6,12-trione

Chemical Property of (7E,13E)-(4R,9R,10S,16S)-9-Benzyloxy-4,10,16-trimethyl-1,5,11-trioxa-cyclohexadeca-7,13-diene-2,6,12-trione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (7E,13E)-(4R,9R,10S,16S)-9-Benzyloxy-4,10,16-trimethyl-1,5,11-trioxa-cyclohexadeca-7,13-diene-2,6,12-trione

There total 10 articles about (7E,13E)-(4R,9R,10S,16S)-9-Benzyloxy-4,10,16-trimethyl-1,5,11-trioxa-cyclohexadeca-7,13-diene-2,6,12-trione 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: 76.0%

(E)-(4R,5S)-4-Benzyloxy-5-[(E)-(S)-5-((R)-3-hydroxy-butyryloxy)-hex-2-enoyloxy]-hex-2-enoic acid (455934-74-4) → (7E,13E)-(4R,9R,10S,16S)-9-Benzyloxy-4,10,16-trimethyl-1,5,11-trioxa-cyclohexadeca-7,13-diene-2,6,12-trione (455934-75-5)

Guidance literature:

(E)-(4R,5S)-4-Benzyloxy-5-[(E)-(S)-5-((R)-3-hydroxy-butyryloxy)-hex-2-enoyloxy]-hex-2-enoic acid; With 2,4,6-trichlorobenzoyl chloride; triethylamine; In tetrahydrofuran; at 20 ℃; for 1.5h;

With dmap; In tetrahydrofuran; toluene; at 100 ℃; for 3h;

DOI:10.1016/S0957-4166(02)00180-5

Reference yield:

(S,E)-5-((tert-butyldimethylsilyl)oxy)hex-2-enoic acid (133522-12-0) → (7E,13E)-(4R,9R,10S,16S)-9-Benzyloxy-4,10,16-trimethyl-1,5,11-trioxa-cyclohexadeca-7,13-diene-2,6,12-trione (455934-75-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 67 percent / DCC; DMAP / CH₂Cl₂ / 24 h / 20 °C

2.1: 93 percent / AcOH; H₂O / tetrahydrofuran / 5 h / 80 °C

3.1: 88 percent / DCC; DMAP; (+)-CSA / CH₂Cl₂ / 1 h / 20 °C

4.1: 93 percent / AcOH; H₂O / tetrahydrofuran / 3 h / 80 °C

5.1: 90 percent / AcOH; AcONa; Zn / tetrahydrofuran / 3 h / 20 °C

6.1: Et₃N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1.5 h / 20 °C

6.2: 76 percent / DMAP / tetrahydrofuran; toluene / 3 h / 100 °C

With dmap; 2,4,6-trichlorobenzoyl chloride; (1S)-10-camphorsulfonic acid; water; sodium acetate; acetic acid; triethylamine; dicyclohexyl-carbodiimide; zinc; In tetrahydrofuran; dichloromethane; 6.1: Yamaguchi macrolactonization / 6.2: Yamaguchi macrolactonization;

DOI:10.1016/S0957-4166(02)00180-5

Reference yield:

methyl (2E,5S)-5-{[tert-butyl(dimethyl)silyl]oxy}-2-hexenoate (133522-08-4) → (7E,13E)-(4R,9R,10S,16S)-9-Benzyloxy-4,10,16-trimethyl-1,5,11-trioxa-cyclohexadeca-7,13-diene-2,6,12-trione (455934-75-5)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 95 percent / aq. NaOH / methanol / 12 h / 20 °C

2.1: 67 percent / DCC; DMAP / CH₂Cl₂ / 24 h / 20 °C

3.1: 93 percent / AcOH; H₂O / tetrahydrofuran / 5 h / 80 °C

4.1: 88 percent / DCC; DMAP; (+)-CSA / CH₂Cl₂ / 1 h / 20 °C

5.1: 93 percent / AcOH; H₂O / tetrahydrofuran / 3 h / 80 °C

6.1: 90 percent / AcOH; AcONa; Zn / tetrahydrofuran / 3 h / 20 °C

7.1: Et₃N; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 1.5 h / 20 °C

7.2: 76 percent / DMAP / tetrahydrofuran; toluene / 3 h / 100 °C

With dmap; sodium hydroxide; 2,4,6-trichlorobenzoyl chloride; (1S)-10-camphorsulfonic acid; water; sodium acetate; acetic acid; triethylamine; dicyclohexyl-carbodiimide; zinc; In tetrahydrofuran; methanol; dichloromethane; 7.1: Yamaguchi macrolactonization / 7.2: Yamaguchi macrolactonization;

DOI:10.1016/S0957-4166(02)00180-5

upstream raw materials:

(E)-(4R,5S)-4-Benzyloxy-5-[(E)-(S)-5-((R)-3-hydroxy-butyryloxy)-hex-2-enoyloxy]-hex-2-enoic acid

(S,E)-5-((tert-butyldimethylsilyl)oxy)hex-2-enoic acid

methyl (2E,5S)-5-{[tert-butyl(dimethyl)silyl]oxy}-2-hexenoate

(E)-(4R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-4-methanesulfonyloxy-hex-2-enoic acid methyl ester