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

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Chemical Name:(6E,10E)-(2S,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-11-(2-methyl-thiazol-4-yl)-6-trityloxymethyl-undeca-6,10-dienal
CAS No.:226940-45-0
Molecular Formula:C₄₂H₅₃NO₃SSi
Molecular Weight:680.039
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-dienal

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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-dienal

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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-dienal

There total 15 articles about (6E,10E)-(2S,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-11-(2-methyl-thiazol-4-yl)-6-trityloxymethyl-undeca-6,10-dienal 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:

: 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

: 226940-45-0
(6E,10E)-(2S,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-11-(2-methyl-thiazol-4-yl)-6-trityloxymethyl-undeca-6,10-dienal

Guidance literature:: With pyridine-SO₃ complex; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; at 0 ℃; for 1h;
DOI:10.1039/a809954e

Reference yield:

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

: 226940-45-0
(6E,10E)-(2S,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-11-(2-methyl-thiazol-4-yl)-6-trityloxymethyl-undeca-6,10-dienal

Guidance literature:: Multi-step reaction with 9 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

9: 4.1 g / SO₃*py; Et₃N / dimethylsulfoxide; CH₂Cl₂ / 1 h / 0 °C

With pyridine; 1H-imidazole; dmap; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; pyridine-SO₃ complex; water; diisobutylaluminium hydride; pyridine hydrogenfluoride; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; 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 / 9: Oxidation;
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

: 226940-45-0
(6E,10E)-(2S,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-11-(2-methyl-thiazol-4-yl)-6-trityloxymethyl-undeca-6,10-dienal

Guidance literature:: Multi-step reaction with 8 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

8: 4.1 g / SO₃*py; Et₃N / dimethylsulfoxide; CH₂Cl₂ / 1 h / 0 °C

With pyridine; 1H-imidazole; dmap; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; pyridine-SO₃ complex; water; diisobutylaluminium hydride; pyridine hydrogenfluoride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; tert-butyl alcohol; benzene; 1: Etherification / 2: Addition / 3: Oxidation / 4: Condensation / 5: Reduction / 6: Etherification / 7: Silyl ether cleavage / 8: Oxidation;
DOI:10.1002/1521-3765(20000804)6:15<2783::AID-CHEM2783>3.0.CO;2-B