(3S,4S,5S,6E,8E,10E)-3-((tert-Butyldiphenylsilyl)oxy)-5-hydroxy-4,6,10-trimethyl-11-(2'-methyloxazol-4'-yl)-6,8,10-undecatrienoic acid 1,5-lactone

Base Information

Chemical Name:(3S,4S,5S,6E,8E,10E)-3-((tert-Butyldiphenylsilyl)oxy)-5-hydroxy-4,6,10-trimethyl-11-(2'-methyloxazol-4'-yl)-6,8,10-undecatrienoic acid 1,5-lactone
CAS No.:139655-31-5
Molecular Formula:C₃₄H₄₁NO₄Si
Molecular Weight:555.789
Hs Code.:

Synonyms:(3S,4S,5S,6E,8E,10E)-3-((tert-Butyldiphenylsilyl)oxy)-5-hydroxy-4,6,10-trimethyl-11-(2'-methyloxazol-4'-yl)-6,8,10-undecatrienoic acid 1,5-lactone

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Chemical Property of (3S,4S,5S,6E,8E,10E)-3-((tert-Butyldiphenylsilyl)oxy)-5-hydroxy-4,6,10-trimethyl-11-(2'-methyloxazol-4'-yl)-6,8,10-undecatrienoic acid 1,5-lactone

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Technology Process of (3S,4S,5S,6E,8E,10E)-3-((tert-Butyldiphenylsilyl)oxy)-5-hydroxy-4,6,10-trimethyl-11-(2'-methyloxazol-4'-yl)-6,8,10-undecatrienoic acid 1,5-lactone

There total 18 articles about (3S,4S,5S,6E,8E,10E)-3-((tert-Butyldiphenylsilyl)oxy)-5-hydroxy-4,6,10-trimethyl-11-(2'-methyloxazol-4'-yl)-6,8,10-undecatrienoic acid 1,5-lactone 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: 51.0%

: 139655-30-4
(6E,8E,10E)-(3S,4R,5S)-3-(tert-Butyl-diphenyl-silanyloxy)-5-hydroxy-4,6,10-trimethyl-11-(2-methyl-oxazol-4-yl)-undeca-6,8,10-trienoic acid

: 139655-31-5
(3S,4S,5S,6E,8E,10E)-3-((tert-Butyldiphenylsilyl)oxy)-5-hydroxy-4,6,10-trimethyl-11-(2'-methyloxazol-4'-yl)-6,8,10-undecatrienoic acid 1,5-lactone

Guidance literature:: With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 23 ℃; for 20h;
DOI:10.1021/jo00034a010

Reference yield:

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

: 139655-31-5
(3S,4S,5S,6E,8E,10E)-3-((tert-Butyldiphenylsilyl)oxy)-5-hydroxy-4,6,10-trimethyl-11-(2'-methyloxazol-4'-yl)-6,8,10-undecatrienoic acid 1,5-lactone

Guidance literature:: Multi-step reaction with 11 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: 58 percent / diisobutylaluminum hydride / diethyl ether; hexane / 6 h / -78 °C

11: 51 percent / EDCI / CH₂Cl₂ / 20 h / 23 °C

With manganese(IV) oxide; sodium periodate; sodium dihydrogenphosphate; 2-methyl-but-2-ene; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 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

: 139655-31-5
(3S,4S,5S,6E,8E,10E)-3-((tert-Butyldiphenylsilyl)oxy)-5-hydroxy-4,6,10-trimethyl-11-(2'-methyloxazol-4'-yl)-6,8,10-undecatrienoic acid 1,5-lactone

Guidance literature:: Multi-step reaction with 10 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: 58 percent / diisobutylaluminum hydride / diethyl ether; hexane / 6 h / -78 °C

10: 51 percent / EDCI / CH₂Cl₂ / 20 h / 23 °C

With manganese(IV) oxide; sodium periodate; sodium dihydrogenphosphate; 2-methyl-but-2-ene; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In 1,4-dioxane; diethyl ether; hexane; dichloromethane; water; acetonitrile; tert-butyl alcohol; benzene;
DOI:10.1021/jo00034a010