Oxacyclohexadec-13-ene-2,6-dione, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-8-hydroxy-5,5,7,9,13-pentameth yl-16-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-, (4S,7R,8S,9S,13Z,16S)-

Base Information

• Chemical Name: Oxacyclohexadec-13-ene-2,6-dione, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-8-hydroxy-5,5,7,9,13-pentameth yl-16-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-, (4S,7R,8S,9S,13Z,16S)-
• CAS No.: 219823-99-1
• Molecular Formula: C33H55NO5SSi
• Molecular Weight: 605.955
• Mol file: 219823-99-1.mol

Synonyms:

Chemical Property of Oxacyclohexadec-13-ene-2,6-dione, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-8-hydroxy-5,5,7,9,13-pentameth yl-16-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-, (4S,7R,8S,9S,13Z,16S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Oxacyclohexadec-13-ene-2,6-dione, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-8-hydroxy-5,5,7,9,13-pentameth yl-16-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-, (4S,7R,8S,9S,13Z,16S)-

There total 1 articles about Oxacyclohexadec-13-ene-2,6-dione, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-8-hydroxy-5,5,7,9,13-pentameth yl-16-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-, (4S,7R,8S,9S,13Z,16S)- 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:

ethyl 2-methylthiazole-4-carboxylate (6436-59-5) → (13Z,4S,7R,8S,9S,16S)-4-(tert-butyldimethylsilyloxy)-8-hydroxy-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methylthiazol-4-yl)vinyl]oxacyclohexadec-13-ene-2,6-dione (219823-99-1)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 84 percent / LiAlH₄ / diethyl ether / 3 h / -78 °C

2.1: 85 percent / Ph₃P; CBr₄ / CCl₄ / 3 h / 20 °C

3.1: 86 percent / 3 h / 160 °C

4.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C

4.2: 86 percent / tetrahydrofuran; hexane / 12 h / -78 - 20 °C

5.1: (1R)-(+)-pinene; BH₃*DMS / tetrahydrofuran / 0.5 h / 20 °C

5.2: 78 percent / lithium hydroxide; sodium perborate / tetrahydrofuran; H₂O / 2 h / 20 °C

6.1: 94 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 0 °C

7.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C

7.2: 59 percent / ZnCl₂ / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C

8.1: pyridine / CH₂Cl₂ / 1 h / 0 °C

9.1: CH₂Cl₂ / 5 h / 20 °C

10.1: 0.67 g / acetic acid / tetrahydrofuran; H₂O / 3 h / 0 °C

11.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C

12.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C

12.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C

13.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating

With pyridine; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; nitromethane; n-butanethiol; carbon tetrabromide; dimethylsulfide borane complex; (1R)-(+)-pinene; 2,4,6-trichlorobenzoyl chloride; ammonium chloride; acetic acid; dimethyl sulfoxide; triethylamine; diisopropylamine; triphenylphosphine; magnesium bromide; zinc; In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; hexane; dichloromethane; water; 4.2: Wadsworth-Horner-Emmons reaction / 6.1: Swern oxidation / 12.2: Yamaguchi macrolactonization;

DOI:10.1021/jo048742o

Reference yield: 95.0%

(13Z,4S,7R,8S,9S,16S)-4-(tert-butyldimethylsilyloxy)-8-hydroxy-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methylthiazol-4-yl)vinyl]oxacyclohexadec-13-ene-2,6-dione (219823-99-1) → epothilone D (189453-10-9)

Guidance literature:

With pyridine hydrogenfluoride; In tetrahydrofuran; at 20 ℃; for 16h;

DOI:10.1021/jo048742o

Reference yield:

(13Z,4S,7R,8S,9S,16S)-4-(tert-butyldimethylsilyloxy)-8-hydroxy-5,5,7,9,13-pentamethyl-16-[(E)-1-methyl-2-(2-methylthiazol-4-yl)vinyl]oxacyclohexadec-13-ene-2,6-dione (219823-99-1) → epothilone B (152044-54-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C

2: 30 percent / m-CPBA / CHCl₃ / 5 h / -10 - 0 °C

With pyridine hydrogenfluoride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; chloroform;

DOI:10.1021/jo048742o

upstream raw materials:

ethyl 2-methylthiazole-4-carboxylate

Downstream raw materials:

epothilone D

epothilone B