Methyl (3S,4S,6E,8E,10E)-3-((tert-butyldiphenylsilyl)oxy)-4,6,10-trimethyl-11-(2'-methyloxazol-4'-yl)-5-oxo-6,8,10-undecatrienoate

Base Information

Chemical Name:Methyl (3S,4S,6E,8E,10E)-3-((tert-butyldiphenylsilyl)oxy)-4,6,10-trimethyl-11-(2'-methyloxazol-4'-yl)-5-oxo-6,8,10-undecatrienoate
CAS No.:139631-20-2
Molecular Formula:C₃₅H₄₃NO₅Si
Molecular Weight:585.816
Hs Code.:

Synonyms:

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Chemical Property of Methyl (3S,4S,6E,8E,10E)-3-((tert-butyldiphenylsilyl)oxy)-4,6,10-trimethyl-11-(2'-methyloxazol-4'-yl)-5-oxo-6,8,10-undecatrienoate

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Technology Process of Methyl (3S,4S,6E,8E,10E)-3-((tert-butyldiphenylsilyl)oxy)-4,6,10-trimethyl-11-(2'-methyloxazol-4'-yl)-5-oxo-6,8,10-undecatrienoate

There total 17 articles about Methyl (3S,4S,6E,8E,10E)-3-((tert-butyldiphenylsilyl)oxy)-4,6,10-trimethyl-11-(2'-methyloxazol-4'-yl)-5-oxo-6,8,10-undecatrienoate 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:

: 10200-43-8
2-methyl-4-carbethoxy-1,3-oxazole

: 139631-20-2
Methyl (3S,4S,6E,8E,10E)-3-((tert-butyldiphenylsilyl)oxy)-4,6,10-trimethyl-11-(2'-methyloxazol-4'-yl)-5-oxo-6,8,10-undecatrienoate

Guidance literature:: Multi-step reaction with 10 steps

1: 56 percent / diisobutylaluminum hydride / diethyl ether; hexane / 0.21 h / -78 °C

2: 85 percent / benzene / 22 h / 80 °C

3: 1.) NaH / 1.) toluene, oil, 40 deg C, 1.5 h, 2.) 110 deg C, 24 h

4: 89 percent / diisobutylaluminum hydride / diethyl ether; hexane / 1.5 h / -78 °C

5: 88 percent / MnO₂ / CH₂Cl₂ / 20 h / 0 to 23 deg C gradually

6: 1.) NaH / 1.) THF, oil, -35 to -10 deg C, 30 min, then to 0 deg C, 1 h, then 22 deg C, 30 min, 2.) -35 to 23, 17 h

7: 83 percent / pyridinium p-toluenesulfonate / diethyl ether / 50 °C

8: 87 percent / NaIO₄ / dioxane; H₂O / 10.5 h / 25 °C

9: NaOCl₂, NaH₂PO₄, 2-methyl-2-butene / acetonitrile; 2-methyl-propan-2-ol; H₂O / 0.25 h / 0 °C

10: diethyl ether

With manganese(IV) oxide; sodium periodate; sodium dihydrogenphosphate; 2-methyl-but-2-ene; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; In 1,4-dioxane; diethyl ether; hexane; dichloromethane; water; acetonitrile; tert-butyl alcohol; benzene;
DOI:10.1021/jo00034a010

Reference yield:

: 113732-84-6
2-methyl-1,3-oxazole-4-carbaldehyde

: 139631-20-2
Methyl (3S,4S,6E,8E,10E)-3-((tert-butyldiphenylsilyl)oxy)-4,6,10-trimethyl-11-(2'-methyloxazol-4'-yl)-5-oxo-6,8,10-undecatrienoate

Guidance literature:: Multi-step reaction with 9 steps

1: 85 percent / benzene / 22 h / 80 °C

2: 1.) NaH / 1.) toluene, oil, 40 deg C, 1.5 h, 2.) 110 deg C, 24 h

3: 89 percent / diisobutylaluminum hydride / diethyl ether; hexane / 1.5 h / -78 °C

4: 88 percent / MnO₂ / CH₂Cl₂ / 20 h / 0 to 23 deg C gradually

5: 1.) NaH / 1.) THF, oil, -35 to -10 deg C, 30 min, then to 0 deg C, 1 h, then 22 deg C, 30 min, 2.) -35 to 23, 17 h

6: 83 percent / pyridinium p-toluenesulfonate / diethyl ether / 50 °C

7: 87 percent / NaIO₄ / dioxane; H₂O / 10.5 h / 25 °C

8: NaOCl₂, NaH₂PO₄, 2-methyl-2-butene / acetonitrile; 2-methyl-propan-2-ol; H₂O / 0.25 h / 0 °C

9: diethyl ether

With manganese(IV) oxide; sodium periodate; sodium dihydrogenphosphate; 2-methyl-but-2-ene; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; In 1,4-dioxane; diethyl ether; hexane; dichloromethane; water; acetonitrile; tert-butyl alcohol; benzene;
DOI:10.1021/jo00034a010

Reference yield:

: 139630-91-4
(E)-2-methyl-3-(2-methyloxazol-4-yl)acrylaldehyde

: 139631-20-2
Methyl (3S,4S,6E,8E,10E)-3-((tert-butyldiphenylsilyl)oxy)-4,6,10-trimethyl-11-(2'-methyloxazol-4'-yl)-5-oxo-6,8,10-undecatrienoate

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) NaH / 1.) toluene, oil, 40 deg C, 1.5 h, 2.) 110 deg C, 24 h

2: 89 percent / diisobutylaluminum hydride / diethyl ether; hexane / 1.5 h / -78 °C

3: 88 percent / MnO₂ / CH₂Cl₂ / 20 h / 0 to 23 deg C gradually

4: 1.) NaH / 1.) THF, oil, -35 to -10 deg C, 30 min, then to 0 deg C, 1 h, then 22 deg C, 30 min, 2.) -35 to 23, 17 h

5: 83 percent / pyridinium p-toluenesulfonate / diethyl ether / 50 °C

6: 87 percent / NaIO₄ / dioxane; H₂O / 10.5 h / 25 °C

7: NaOCl₂, NaH₂PO₄, 2-methyl-2-butene / acetonitrile; 2-methyl-propan-2-ol; H₂O / 0.25 h / 0 °C

8: diethyl ether

With manganese(IV) oxide; sodium periodate; sodium dihydrogenphosphate; 2-methyl-but-2-ene; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; In 1,4-dioxane; diethyl ether; hexane; dichloromethane; water; acetonitrile; tert-butyl alcohol;
DOI:10.1021/jo00034a010