(7E,13E)-(4R,10S,15R,16S)-15-Benzyloxy-4,10,16-trimethyl-1,5,11-trioxa-cyclohexadeca-7,13-diene-2,6,12-trione

Base Information

Chemical Name:(7E,13E)-(4R,10S,15R,16S)-15-Benzyloxy-4,10,16-trimethyl-1,5,11-trioxa-cyclohexadeca-7,13-diene-2,6,12-trione
CAS No.:455934-70-0
Molecular Formula:C₂₃H₂₈O₇
Molecular Weight:416.471
Hs Code.:

Synonyms:

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Chemical Property of (7E,13E)-(4R,10S,15R,16S)-15-Benzyloxy-4,10,16-trimethyl-1,5,11-trioxa-cyclohexadeca-7,13-diene-2,6,12-trione

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Technology Process of (7E,13E)-(4R,10S,15R,16S)-15-Benzyloxy-4,10,16-trimethyl-1,5,11-trioxa-cyclohexadeca-7,13-diene-2,6,12-trione

There total 11 articles about (7E,13E)-(4R,10S,15R,16S)-15-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:

: 455934-69-7
(E)-(4R,5S)-4-Benzyloxy-5-[(R)-3-((E)-(S)-5-hydroxy-hex-2-enoyloxy)-butyryloxy]-hex-2-enoic acid

: 455934-70-0
(7E,13E)-(4R,10S,15R,16S)-15-Benzyloxy-4,10,16-trimethyl-1,5,11-trioxa-cyclohexadeca-7,13-diene-2,6,12-trione

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

With dmap; In tetrahydrofuran; toluene; at 100 ℃; for 3.5h;
DOI:10.1016/S0957-4166(02)00180-5

Reference yield:

: 133522-12-0
(S,E)-5-((tert-butyldimethylsilyl)oxy)hex-2-enoic acid

: 455934-70-0
(7E,13E)-(4R,10S,15R,16S)-15-Benzyloxy-4,10,16-trimethyl-1,5,11-trioxa-cyclohexadeca-7,13-diene-2,6,12-trione

Guidance literature:: Multi-step reaction with 4 steps

1.1: 55 percent / DCC; DMAP / CH₂Cl₂ / 24 h / 20 °C

2.1: 86 percent / AcOH; H₂O / tetrahydrofuran / 12 h / 80 °C

3.1: 100 percent / AcOH; AcONa; Zn / tetrahydrofuran / 3 h / 20 °C

4.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 2 h / 20 °C

4.2: 0.067 g / DMAP / tetrahydrofuran; toluene / 3.5 h / 100 °C

With dmap; 2,4,6-trichlorobenzoyl chloride; water; sodium acetate; acetic acid; triethylamine; dicyclohexyl-carbodiimide; zinc; In tetrahydrofuran; dichloromethane; 4.1: Yamaguchi macrolactonization / 4.2: Yamaguchi macrolactonization;
DOI:10.1016/S0957-4166(02)00180-5

Reference yield:

: 133522-08-4
methyl (2E,5S)-5-{[tert-butyl(dimethyl)silyl]oxy}-2-hexenoate

: 455934-70-0
(7E,13E)-(4R,10S,15R,16S)-15-Benzyloxy-4,10,16-trimethyl-1,5,11-trioxa-cyclohexadeca-7,13-diene-2,6,12-trione

Guidance literature:: Multi-step reaction with 5 steps

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

2.1: 55 percent / DCC; DMAP / CH₂Cl₂ / 24 h / 20 °C

3.1: 86 percent / AcOH; H₂O / tetrahydrofuran / 12 h / 80 °C

4.1: 100 percent / AcOH; AcONa; Zn / tetrahydrofuran / 3 h / 20 °C

5.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 2 h / 20 °C

5.2: 0.067 g / DMAP / tetrahydrofuran; toluene / 3.5 h / 100 °C

With dmap; sodium hydroxide; 2,4,6-trichlorobenzoyl chloride; water; sodium acetate; acetic acid; triethylamine; dicyclohexyl-carbodiimide; zinc; In tetrahydrofuran; methanol; dichloromethane; 5.1: Yamaguchi macrolactonization / 5.2: Yamaguchi macrolactonization;
DOI:10.1016/S0957-4166(02)00180-5