(6R)-(tert-butyl-dimethyl-silanyloxy)-2,(10S)-dimethyl-1-(2-methyl-thiazol-4-yl)-11-(triisopropyl-silanyloxy)-undec-(1E)-en-(3S,5R)-diol

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Chemical Name:(6R)-(tert-butyl-dimethyl-silanyloxy)-2,(10S)-dimethyl-1-(2-methyl-thiazol-4-yl)-11-(triisopropyl-silanyloxy)-undec-(1E)-en-(3S,5R)-diol
CAS No.:342607-15-2
Molecular Formula:C₃₂H₆₃NO₄SSi₂
Molecular Weight:614.094
Hs Code.:

Synonyms:(6R)-(tert-butyl-dimethyl-silanyloxy)-2,(10S)-dimethyl-1-(2-methyl-thiazol-4-yl)-11-(triisopropyl-silanyloxy)-undec-(1E)-en-(3S,5R)-diol

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Chemical Property of (6R)-(tert-butyl-dimethyl-silanyloxy)-2,(10S)-dimethyl-1-(2-methyl-thiazol-4-yl)-11-(triisopropyl-silanyloxy)-undec-(1E)-en-(3S,5R)-diol

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Technology Process of (6R)-(tert-butyl-dimethyl-silanyloxy)-2,(10S)-dimethyl-1-(2-methyl-thiazol-4-yl)-11-(triisopropyl-silanyloxy)-undec-(1E)-en-(3S,5R)-diol

There total 1 articles about (6R)-(tert-butyl-dimethyl-silanyloxy)-2,(10S)-dimethyl-1-(2-methyl-thiazol-4-yl)-11-(triisopropyl-silanyloxy)-undec-(1E)-en-(3S,5R)-diol 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

: 342607-15-2
(6R)-(tert-butyl-dimethyl-silanyloxy)-2,(10S)-dimethyl-1-(2-methyl-thiazol-4-yl)-11-(triisopropyl-silanyloxy)-undec-(1E)-en-(3S,5R)-diol

Guidance literature:: Multi-step reaction with 5 steps

1: DIBAL-H / CH₂Cl₂ / 5.5 h / -78 °C

2: 80 percent / DBU; LiCl / acetonitrile / 20 °C

3: SmI₂ / tetrahydrofuran / 0.25 h / 0 °C

4: 146 mg / B(OH)3; H₂O / tetrahydrofuran / 0.5 h / 20 °C

5: 90 percent / NaBH₄; Et₃B / methanol; tetrahydrofuran / 6 h / -78 °C

With sodium tetrahydroborate; samarium diiodide; triethyl borane; water; boric acid; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;
DOI:10.1021/jo015791h

Reference yield:

: 342607-15-2
(6R)-(tert-butyl-dimethyl-silanyloxy)-2,(10S)-dimethyl-1-(2-methyl-thiazol-4-yl)-11-(triisopropyl-silanyloxy)-undec-(1E)-en-(3S,5R)-diol

: 152044-53-6
epithilone A

Guidance literature:: Multi-step reaction with 14 steps

1.1: NEt₃; SOCl₂ / CH₂Cl₂ / 0.33 h / 0 °C

2.1: 122 mg / BuNF*3H₂O / tetrahydrofuran / 2 h / Heating

3.1: 75 percent / Et₃N; DMAP / CH₂Cl₂ / 0 - 20 °C

4.1: aq. AcOH / tetrahydrofuran / 3.5 h / 30 °C

5.1: 101 mg / TPAP; NMO; molecular sieves / CH₂Cl₂ / 0.33 h

6.1: LDA / tetrahydrofuran / 0.58 h / -78 - -40 °C

6.2: 86 percent / tetrahydrofuran / 1 h / -78 °C

7.1: 91 percent / pyridine / CH₂Cl₂ / 2 h

8.1: 86 percent / OsO₄; NMO / 2-methyl-propan-2-ol; tetrahydrofuran; H₂O / 18 h / 20 °C

9.1: 98.0 mg / Pb(OAc)4 / ethyl acetate / 0 °C

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

11.1: 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

12.1: 2,4,6-trichlorobenzoyl chloride; Et₃N / tetrahydrofuran / 0.5 h / 0 °C

12.2: 74 percent / DMAP / tetrahydrofuran; toluene / 3 h

13.1: 82 percent / Zn; NH₄Cl / methanol / 0.08 h / 20 °C

14.1: 38 percent / HF*pyridine / 168 h / 35 - 40 °C

With pyridine; lead(IV) acetate; dmap; sodium chlorite; disodium hydrogenphosphate; osmium(VIII) oxide; thionyl chloride; N-methyl-2-indolinone; molecular sieve; tetrapropylammonium perruthennate; 2-methyl-but-2-ene; 2,4,6-trichlorobenzoyl chloride; tetrabutyl ammonium fluoride; ammonium chloride; pyridine hydrogenfluoride; acetic acid; triethylamine; citric acid; zinc; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; tert-butyl alcohol; 6.2: Mulzer's aldol coupling;
DOI:10.1021/ja0155635