(7S)-(tert-butyl-dimethyl-silanyloxy)-(11S)-hydroxy-8,8,(10R,12S)-tetramethyl-(3S)-[1-methyl-(2E)-(2-methyl-thiazol-4-yl)-vinyl]-4,17-dioxa-bicyclo[14.1.0]heptadecane-5,9-dione

Base Information

Chemical Name:(7S)-(tert-butyl-dimethyl-silanyloxy)-(11S)-hydroxy-8,8,(10R,12S)-tetramethyl-(3S)-[1-methyl-(2E)-(2-methyl-thiazol-4-yl)-vinyl]-4,17-dioxa-bicyclo[14.1.0]heptadecane-5,9-dione
CAS No.:342607-36-7
Molecular Formula:C₃₂H₅₃NO₆SSi
Molecular Weight:607.927
Hs Code.:

(7S)-(tert-butyl-dimethyl-silanyloxy)-(11S)-hydroxy-8,8,(10R,12S)-tetramethyl-(3S)-[1-methyl-(2E)-(2-methyl-thiazol-4-yl)-vinyl]-4,17-dioxa-bicyclo[14.1.0]heptadecane-5,9-dione

Synonyms:(7S)-(tert-butyl-dimethyl-silanyloxy)-(11S)-hydroxy-8,8,(10R,12S)-tetramethyl-(3S)-[1-methyl-(2E)-(2-methyl-thiazol-4-yl)-vinyl]-4,17-dioxa-bicyclo[14.1.0]heptadecane-5,9-dione

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Chemical Property of (7S)-(tert-butyl-dimethyl-silanyloxy)-(11S)-hydroxy-8,8,(10R,12S)-tetramethyl-(3S)-[1-methyl-(2E)-(2-methyl-thiazol-4-yl)-vinyl]-4,17-dioxa-bicyclo[14.1.0]heptadecane-5,9-dione

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Technology Process of (7S)-(tert-butyl-dimethyl-silanyloxy)-(11S)-hydroxy-8,8,(10R,12S)-tetramethyl-(3S)-[1-methyl-(2E)-(2-methyl-thiazol-4-yl)-vinyl]-4,17-dioxa-bicyclo[14.1.0]heptadecane-5,9-dione

There total 1 articles about (7S)-(tert-butyl-dimethyl-silanyloxy)-(11S)-hydroxy-8,8,(10R,12S)-tetramethyl-(3S)-[1-methyl-(2E)-(2-methyl-thiazol-4-yl)-vinyl]-4,17-dioxa-bicyclo[14.1.0]heptadecane-5,9-dione 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

: 342607-36-7
(7S)-(tert-butyl-dimethyl-silanyloxy)-(11S)-hydroxy-8,8,(10R,12S)-tetramethyl-(3S)-[1-methyl-(2E)-(2-methyl-thiazol-4-yl)-vinyl]-4,17-dioxa-bicyclo[14.1.0]heptadecane-5,9-dione

Guidance literature:: Multi-step reaction with 18 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

15.1: HF*pyridine / pyridine; tetrahydrofuran / 0 - 20 °C

16.1: 63.2 mg / NaClO₂; 2-methyl-2-butene / 2-methyl-propan-2-ol; aq. phosphate buffer / 1.5 h / 0 °C

17.1: 2,4,6-trichlorobenzoyl chloride; Et₃N

17.2: 74 percent / 4-dimethylaminopyridine

18.1: 82 percent / Zn; NH₄Cl / methanol / 0.08 h / 20 °C

With pyridine; lead(IV) acetate; dmap; sodium chlorite; sodium tetrahydroborate; osmium(VIII) oxide; thionyl chloride; N-methyl-2-indolinone; samarium diiodide; 2-methyl-but-2-ene; triethyl borane; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; water; boric acid; diisobutylaluminium hydride; ammonium chloride; pyridine hydrogenfluoride; triethylamine; lithium hexamethyldisilazane; zinc; lithium diisopropyl amide; In tetrahydrofuran; pyridine; methanol; phosphate buffer; dichloromethane; water; ethyl acetate; tert-butyl alcohol; 16.1: Lindgrin oxidation;
DOI:10.1021/jo015791h