(6E,10E)-(2S,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-11-(2-methyl-thiazol-4-yl)-6-trityloxymethyl-undeca-6,10-dien-1-ol

Base Information

Chemical Name:(6E,10E)-(2S,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-11-(2-methyl-thiazol-4-yl)-6-trityloxymethyl-undeca-6,10-dien-1-ol
CAS No.:226940-44-9
Molecular Formula:C₄₂H₅₅NO₃SSi
Molecular Weight:682.055
Hs Code.:

Synonyms:(6E,10E)-(2S,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-11-(2-methyl-thiazol-4-yl)-6-trityloxymethyl-undeca-6,10-dien-1-ol

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Chemical Property of (6E,10E)-(2S,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-11-(2-methyl-thiazol-4-yl)-6-trityloxymethyl-undeca-6,10-dien-1-ol

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Technology Process of (6E,10E)-(2S,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-11-(2-methyl-thiazol-4-yl)-6-trityloxymethyl-undeca-6,10-dien-1-ol

There total 14 articles about (6E,10E)-(2S,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-11-(2-methyl-thiazol-4-yl)-6-trityloxymethyl-undeca-6,10-dien-1-ol 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: 66.0%

: 226940-43-8
4-[(1E,5E)-(3S,10S)-3,11-Bis-(tert-butyl-dimethyl-silanyloxy)-10-methyl-6-trityloxymethyl-undeca-1,5-dienyl]-2-methyl-thiazole

: 226940-44-9
(6E,10E)-(2S,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-11-(2-methyl-thiazol-4-yl)-6-trityloxymethyl-undeca-6,10-dien-1-ol

Guidance literature:: With pyridine; pyridine hydrogenfluoride; In tetrahydrofuran; at 25 ℃; for 4h;
DOI:10.1002/1521-3765(20000804)6:15<2783::AID-CHEM2783>3.0.CO;2-B

Reference yield:

: 226940-34-7
(2E)-3-(2-Methylthiazol-4-yl)-2-propenal

: 226940-44-9
(6E,10E)-(2S,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-11-(2-methyl-thiazol-4-yl)-6-trityloxymethyl-undeca-6,10-dien-1-ol

Guidance literature:: Multi-step reaction with 8 steps

1: 17.7 g / diethyl ether; CH₂Cl₂; pentane / 2 h / -100 °C

2: 99 percent / imidazole / dimethylformamide / 2 h / 0 - 25 °C

3: 6.64 g / H₂O; NMO; OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol / 12 h / 0 - 25 °C

4: 5.4 g / aq. NaIO₄ / methanol / 1 h / 0 - 25 °C

5: 84 percent / benzene / 18 h / Heating

6: 93 percent / DIBAL / tetrahydrofuran / 3 h / -78 °C

7: 82 percent / DMAP / dimethylformamide / 24 h / 80 °C

8: 66 percent / HF*py; pyridine / tetrahydrofuran / 4 h / 25 °C

With pyridine; 1H-imidazole; dmap; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; water; diisobutylaluminium hydride; pyridine hydrogenfluoride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; pentane; benzene; 1: Addition / 2: Etherification / 3: Addition / 4: Oxidation / 5: Condensation / 6: Reduction / 7: Etherification / 8: Silyl ether cleavage;
DOI:10.1002/1521-3765(20000804)6:15<2783::AID-CHEM2783>3.0.CO;2-B

Reference yield:

: 226940-35-8
(E)-(S)-1-(2-Methyl-thiazol-4-yl)-hexa-1,5-dien-3-ol

: 226940-44-9
(6E,10E)-(2S,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-11-(2-methyl-thiazol-4-yl)-6-trityloxymethyl-undeca-6,10-dien-1-ol

Guidance literature:: Multi-step reaction with 7 steps

1: 99 percent / imidazole / dimethylformamide / 2 h / 0 - 25 °C

2: 6.64 g / H₂O; NMO; OsO₄ / tetrahydrofuran; 2-methyl-propan-2-ol / 12 h / 0 - 25 °C

3: 5.4 g / aq. NaIO₄ / methanol / 1 h / 0 - 25 °C

4: 84 percent / benzene / 18 h / Heating

5: 93 percent / DIBAL / tetrahydrofuran / 3 h / -78 °C

6: 82 percent / DMAP / dimethylformamide / 24 h / 80 °C

7: 66 percent / HF*py; pyridine / tetrahydrofuran / 4 h / 25 °C

With pyridine; 1H-imidazole; dmap; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; water; diisobutylaluminium hydride; pyridine hydrogenfluoride; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; tert-butyl alcohol; benzene; 1: Etherification / 2: Addition / 3: Oxidation / 4: Condensation / 5: Reduction / 6: Etherification / 7: Silyl ether cleavage;
DOI:10.1002/1521-3765(20000804)6:15<2783::AID-CHEM2783>3.0.CO;2-B