4-[(1E,5E)-(S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-6-trityloxymethyl-nona-1,5,8-trienyl]-2-methyl-thiazole

Base Information

Chemical Name:4-[(1E,5E)-(S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-6-trityloxymethyl-nona-1,5,8-trienyl]-2-methyl-thiazole
CAS No.:201136-65-4
Molecular Formula:C₄₀H₄₉NO₂SSi
Molecular Weight:635.986
Hs Code.:

Synonyms:4-[(1E,5E)-(S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-6-trityloxymethyl-nona-1,5,8-trienyl]-2-methyl-thiazole

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Chemical Property of 4-[(1E,5E)-(S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-6-trityloxymethyl-nona-1,5,8-trienyl]-2-methyl-thiazole

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Technology Process of 4-[(1E,5E)-(S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-6-trityloxymethyl-nona-1,5,8-trienyl]-2-methyl-thiazole

There total 1 articles about 4-[(1E,5E)-(S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-6-trityloxymethyl-nona-1,5,8-trienyl]-2-methyl-thiazole 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: 99.0%

: 76-83-5
trityl chloride

: 193146-41-7
(2E,6E)(5S)-6-methyl-7-(2-methyl-(1,3-thiazol-4-yl))-2-prop-2-enyl-5-(1,1,2,2-tetramethyl-1-silapropoxy)hepta-2,6-dien-1-ol

: 201136-65-4
4-[(1E,5E)-(S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-6-trityloxymethyl-nona-1,5,8-trienyl]-2-methyl-thiazole

Guidance literature:: With dmap; In N,N-dimethyl-formamide; at 70 ℃; for 1h;
DOI:10.1039/a705845d

Reference yield:

: 201136-65-4
4-[(1E,5E)-(S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-6-trityloxymethyl-nona-1,5,8-trienyl]-2-methyl-thiazole

: 201136-67-6
4-[(1E,5E)-(S)-3-(tert-Butyl-dimethyl-silanyloxy)-9-iodo-2-methyl-6-trityloxymethyl-nona-1,5-dienyl]-2-methyl-thiazole

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) 9-BBN, 2.) aq. H₂O₂, aq. NaOH / 1.) THF, 0 deg C, 2 h, 2.) THF, 0 deg C, 0.5 h

2: 90 percent / I₂, PPh₃, imidazole / diethyl ether; acetonitrile / 0.5 h / 0 °C

With 1H-imidazole; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; dihydrogen peroxide; iodine; triphenylphosphine; In diethyl ether; acetonitrile;
DOI:10.1016/S0040-4020(98)00352-4

Reference yield:

: 201136-65-4
4-[(1E,5E)-(S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-6-trityloxymethyl-nona-1,5,8-trienyl]-2-methyl-thiazole

: 201136-70-1
(6E,10E)-(2S,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-2,10-dimethyl-11-(2-methyl-thiazol-4-yl)-6-trityloxymethyl-undeca-6,10-dienal

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) 9-BBN, 2.) aq. H₂O₂, aq. NaOH / 1.) THF, 0 deg C, 2 h, 2.) THF, 0 deg C, 0.5 h

2: 90 percent / I₂, PPh₃, imidazole / diethyl ether; acetonitrile / 0.5 h / 0 °C

3: diisopropylamine, n-BuLi / 1.) THF, hexane, 0 deg C, 14 h, 2.) THF, hexane, -100 to -20 deg C, 10 h

4: 91 percent / monoperoxyphthalic acid magnesium salt / methanol; H₂O; tetrahydrofuran / 1 h / 0 °C

5: 97 percent / DIBAL / toluene / 1 h / -78 °C

With 1H-imidazole; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; dihydrogen peroxide; iodine; diisobutylaluminium hydride; Monoperoxyphthalic acid, magnesium salt; diisopropylamine; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; water; toluene; acetonitrile;
DOI:10.1016/S0040-4020(98)00352-4