(6E,10E)-(2S,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-11-iodo-2,10-dimethyl-6-trityloxymethyl-undeca-6,10-dienenitrile

Base Information

Chemical Name:(6E,10E)-(2S,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-11-iodo-2,10-dimethyl-6-trityloxymethyl-undeca-6,10-dienenitrile
CAS No.:240815-95-6
Molecular Formula:C₃₉H₅₀INO₂Si
Molecular Weight:719.822
Hs Code.:

Synonyms:(6E,10E)-(2S,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-11-iodo-2,10-dimethyl-6-trityloxymethyl-undeca-6,10-dienenitrile

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Chemical Property of (6E,10E)-(2S,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-11-iodo-2,10-dimethyl-6-trityloxymethyl-undeca-6,10-dienenitrile

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Technology Process of (6E,10E)-(2S,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-11-iodo-2,10-dimethyl-6-trityloxymethyl-undeca-6,10-dienenitrile

There total 12 articles about (6E,10E)-(2S,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-11-iodo-2,10-dimethyl-6-trityloxymethyl-undeca-6,10-dienenitrile 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: 89.0%

: 240815-94-5
[(6E,10E)-(2S,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-11-iodo-2,10-dimethyl-6-trityloxymethyl-undeca-6,10-dien-(E)-ylidene]-((S)-2-methoxymethyl-pyrrolidin-1-yl)-amine

: 240815-95-6
(6E,10E)-(2S,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-11-iodo-2,10-dimethyl-6-trityloxymethyl-undeca-6,10-dienenitrile

Guidance literature:: With phosphate buffer; MMPP; In tetrahydrofuran; methanol; at 0 ℃; for 3h;
DOI:10.1016/S0968-0896(98)00153-9

Reference yield:

: 76-83-5
trityl chloride

: 240815-95-6
(6E,10E)-(2S,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-11-iodo-2,10-dimethyl-6-trityloxymethyl-undeca-6,10-dienenitrile

Guidance literature:: Multi-step reaction with 5 steps

1: 95 percent / 4-DMAP / dimethylformamide / 21 h / 80 °C

2: 95 percent / 9-BBN / tetrahydrofuran / 9 h / 0 °C

3: 97 percent / I₂, PPh₃, imidazole / diethyl ether; acetonitrile / 0.75 h / 0 °C

4: 1.) LDA / 1.) THf, hexane, 0 deg C, 16 h, 2.) THf, hexane, -100 deg C to -20 deg C, 20 h

5: 89 percent / MMPP*6H₂O, phosphate buffer / tetrahydrofuran; methanol / 3 h / 0 °C

With 1H-imidazole; dmap; 9-borabicyclo[3.3.1]nonane dimer; phosphate buffer; MMPP; iodine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0968-0896(98)00153-9

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 240815-95-6
(6E,10E)-(2S,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-11-iodo-2,10-dimethyl-6-trityloxymethyl-undeca-6,10-dienenitrile

Guidance literature:: Multi-step reaction with 10 steps

1: 84 percent / imidazole / dimethylformamide / 7 h / 0 - 25 °C

2: 89 percent / OsO₄, NMO / tetrahydrofuran; 2-methyl-propan-2-ol; H₂O / 13 h / 25 °C

3: 92 percent / NaIO₄ / methanol; H₂O / 0.5 h / 25 °C

4: 98 percent / benzene / 1.5 h / Heating

5: 100 percent / DIBAL / tetrahydrofuran; CH₂Cl₂ / 1.33 h / -78 °C

6: 95 percent / 4-DMAP / dimethylformamide / 21 h / 80 °C

7: 95 percent / 9-BBN / tetrahydrofuran / 9 h / 0 °C

8: 97 percent / I₂, PPh₃, imidazole / diethyl ether; acetonitrile / 0.75 h / 0 °C

9: 1.) LDA / 1.) THf, hexane, 0 deg C, 16 h, 2.) THf, hexane, -100 deg C to -20 deg C, 20 h

10: 89 percent / MMPP*6H₂O, phosphate buffer / tetrahydrofuran; methanol / 3 h / 0 °C

With 1H-imidazole; dmap; sodium periodate; osmium(VIII) oxide; 9-borabicyclo[3.3.1]nonane dimer; N-methyl-2-indolinone; phosphate buffer; MMPP; iodine; diisobutylaluminium hydride; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; benzene;
DOI:10.1016/S0968-0896(98)00153-9