carbonic acid (5S)-(tert-butyl-dimethyl-silanyloxy)-(2R),4,4-trimethyl-(1S)-((1R)-methyl-4-{(2S,3R)-[3-methyl-4-(2-methyl-thiazol-4-yl)-(2S)-(triethyl-silanyloxy)-but-(3E)-enyl]-oxiranyl}-butyl)-3,7-dioxo-heptyl ester 2,2,2-trichloro-ethyl ester

Base Information

Chemical Name:carbonic acid (5S)-(tert-butyl-dimethyl-silanyloxy)-(2R),4,4-trimethyl-(1S)-((1R)-methyl-4-{(2S,3R)-[3-methyl-4-(2-methyl-thiazol-4-yl)-(2S)-(triethyl-silanyloxy)-but-(3E)-enyl]-oxiranyl}-butyl)-3,7-dioxo-heptyl ester 2,2,2-trichloro-ethyl ester
CAS No.:342607-35-6
Molecular Formula:C₄₁H₇₀Cl₃NO₈SSi₂
Molecular Weight:899.605
Hs Code.:

carbonic acid (5S)-(tert-butyl-dimethyl-silanyloxy)-(2R),4,4-trimethyl-(1S)-((1R)-methyl-4-{(2S,3R)-[3-methyl-4-(2-methyl-thiazol-4-yl)-(2S)-(triethyl-silanyloxy)-but-(3E)-enyl]-oxiranyl}-butyl)-3,7-dioxo-heptyl ester 2,2,2-trichloro-ethyl ester

Synonyms:carbonic acid (5S)-(tert-butyl-dimethyl-silanyloxy)-(2R),4,4-trimethyl-(1S)-((1R)-methyl-4-{(2S,3R)-[3-methyl-4-(2-methyl-thiazol-4-yl)-(2S)-(triethyl-silanyloxy)-but-(3E)-enyl]-oxiranyl}-butyl)-3,7-dioxo-heptyl ester 2,2,2-trichloro-ethyl ester

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Chemical Property of carbonic acid (5S)-(tert-butyl-dimethyl-silanyloxy)-(2R),4,4-trimethyl-(1S)-((1R)-methyl-4-{(2S,3R)-[3-methyl-4-(2-methyl-thiazol-4-yl)-(2S)-(triethyl-silanyloxy)-but-(3E)-enyl]-oxiranyl}-butyl)-3,7-dioxo-heptyl ester 2,2,2-trichloro-ethyl ester

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Technology Process of carbonic acid (5S)-(tert-butyl-dimethyl-silanyloxy)-(2R),4,4-trimethyl-(1S)-((1R)-methyl-4-{(2S,3R)-[3-methyl-4-(2-methyl-thiazol-4-yl)-(2S)-(triethyl-silanyloxy)-but-(3E)-enyl]-oxiranyl}-butyl)-3,7-dioxo-heptyl ester 2,2,2-trichloro-ethyl ester

There total 1 articles about carbonic acid (5S)-(tert-butyl-dimethyl-silanyloxy)-(2R),4,4-trimethyl-(1S)-((1R)-methyl-4-{(2S,3R)-[3-methyl-4-(2-methyl-thiazol-4-yl)-(2S)-(triethyl-silanyloxy)-but-(3E)-enyl]-oxiranyl}-butyl)-3,7-dioxo-heptyl ester 2,2,2-trichloro-ethyl ester 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:

: 6436-59-5
ethyl 2-methylthiazole-4-carboxylate

: 342607-35-6
carbonic acid (5S)-(tert-butyl-dimethyl-silanyloxy)-(2R),4,4-trimethyl-(1S)-((1R)-methyl-4-{(2S,3R)-[3-methyl-4-(2-methyl-thiazol-4-yl)-(2S)-(triethyl-silanyloxy)-but-(3E)-enyl]-oxiranyl}-butyl)-3,7-dioxo-heptyl ester 2,2,2-trichloro-ethyl ester

Guidance literature:: Multi-step reaction with 14 steps

1.1: DIBAL-H / CH₂Cl₂ / 5.5 h / -78 °C

2.1: LiHMDS / tetrahydrofuran / 0.33 h / -78 °C

2.2: 87 percent / tetrahydrofuran / -78 - 20 °C

3.1: SmI₂ / tetrahydrofuran / 0.33 h / 0 °C

4.1: 114 mg / H₂O; B(OH)3 / tetrahydrofuran / 0.5 h / 20 °C

5.1: 91 percent / Et₃B; NaBH₄ / methanol; tetrahydrofuran / 17 h / -78 °C

6.1: SOCl₂; Et₃N / CH₂Cl₂ / 0.33 h / 0 °C

7.1: 58 mg / Bu₄NF*3H₂O / tetrahydrofuran / 6 h / Heating

8.1: 79 percent / Et₃N; DMAP / CH₂Cl₂ / 15 h / 20 °C

9.1: NMO; OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O / 18 h / 20 °C

10.1: 4.4 mg / Pb(OAc)4 / ethyl acetate / 0.25 h / 0 °C

11.1: 86 percent / LDA / tetrahydrofuran / 1 h / -78 °C

12.1: 91 percent / pyridine / CH₂Cl₂ / 2 h / 0 °C

13.1: NMO; OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O / 18 h / 20 °C

14.1: 98.0 mg / Pb(OAc)4 / ethyl acetate / 0.13 h / 0 °C

With pyridine; lead(IV) acetate; dmap; sodium tetrahydroborate; osmium(VIII) oxide; thionyl chloride; N-methyl-2-indolinone; samarium diiodide; triethyl borane; tetrabutyl ammonium fluoride; water; boric acid; diisobutylaluminium hydride; triethylamine; lithium hexamethyldisilazane; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; tert-butyl alcohol;
DOI:10.1021/jo015791h

Reference yield:

: 342607-35-6
carbonic acid (5S)-(tert-butyl-dimethyl-silanyloxy)-(2R),4,4-trimethyl-(1S)-((1R)-methyl-4-{(2S,3R)-[3-methyl-4-(2-methyl-thiazol-4-yl)-(2S)-(triethyl-silanyloxy)-but-(3E)-enyl]-oxiranyl}-butyl)-3,7-dioxo-heptyl ester 2,2,2-trichloro-ethyl ester

: 152044-53-6
epithilone A

Guidance literature:: Multi-step reaction with 5 steps

1.1: HF*pyridine / tetrahydrofuran / 1.5 h / 20 °C

2.1: 63.2 mg / NaClO₂; 2-methyl-2-butene; aq. citric acid/Na₂HPO₄ / 2-methyl-propan-2-ol / 1.5 h / 0 °C / pH 3.6

3.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 0.5 h / 0 °C

3.2: 74 percent / DMAP / tetrahydrofuran; toluene / 3 h

4.1: 82 percent / Zn; NH₄Cl / methanol / 0.08 h / 20 °C

5.1: 38 percent / HF*pyridine / 168 h / 35 - 40 °C

With sodium chlorite; disodium hydrogenphosphate; 2-methyl-but-2-ene; 2,4,6-trichlorobenzoyl chloride; ammonium chloride; pyridine hydrogenfluoride; triethylamine; citric acid; zinc; In tetrahydrofuran; methanol; tert-butyl alcohol;
DOI:10.1021/ja0155635