Se-phenyl (E,E,E,E,E,E,E)-31-hydroxy-5,9,13,17,21,25,29-heptmethylhentriaconta-5,9,13,17,21,25,29-heptaeneselenoate

Base Information

• Chemical Name: Se-phenyl (E,E,E,E,E,E,E)-31-hydroxy-5,9,13,17,21,25,29-heptmethylhentriaconta-5,9,13,17,21,25,29-heptaeneselenoate
• CAS No.: 229305-90-2
• Molecular Formula: C₄₄H₆₆O₂Se
• Molecular Weight: 705.967

Synonyms:Se-phenyl (E,E,E,E,E,E,E)-31-hydroxy-5,9,13,17,21,25,29-heptmethylhentriaconta-5,9,13,17,21,25,29-heptaeneselenoate

Chemical Property of Se-phenyl (E,E,E,E,E,E,E)-31-hydroxy-5,9,13,17,21,25,29-heptmethylhentriaconta-5,9,13,17,21,25,29-heptaeneselenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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Technology Process of Se-phenyl (E,E,E,E,E,E,E)-31-hydroxy-5,9,13,17,21,25,29-heptmethylhentriaconta-5,9,13,17,21,25,29-heptaeneselenoate

There total 21 articles about Se-phenyl (E,E,E,E,E,E,E)-31-hydroxy-5,9,13,17,21,25,29-heptmethylhentriaconta-5,9,13,17,21,25,29-heptaeneselenoate 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: 94.0%

Se-phenyl (E,E,E,E,E,E,E)-5,9,13,17,21,25,29-heptamethyl-31-[(tetrahydro-2H-pyran-2-yl)oxy]hentriaconta-5,9,13,17,21,25,29-heptaeneselenoate (229305-89-9) → Se-phenyl (E,E,E,E,E,E,E)-31-hydroxy-5,9,13,17,21,25,29-heptmethylhentriaconta-5,9,13,17,21,25,29-heptaeneselenoate (229305-90-2)

Guidance literature:

With sodium hydrogencarbonate; toluene-4-sulfonic acid; In methanol;

DOI:10.1002/1522-2675(20000906)83:9<2629::AID-HLCA2629>3.0.CO;2-W

Reference yield:

((2E,6E)-8-Bromo-3,7-dimethyl-octa-2,6-dienyloxymethyl)-benzene (69297-43-4) → Se-phenyl (E,E,E,E,E,E,E)-31-hydroxy-5,9,13,17,21,25,29-heptmethylhentriaconta-5,9,13,17,21,25,29-heptaeneselenoate (229305-90-2)

Guidance literature:

Multi-step reaction with 18 steps

1: 84 percent / BuLi / hexane; tetrahydrofuran / 4 h / -78 °C

2: Li; EtNH₂ / tetrahydrofuran / 2 h / -78 °C

3: BuLi; 1,3-dimethyl-3,4,5,6-tetrahydropyrimidin-2(1H)-one / hexane; tetrahydrofuran / 3 h / 0 °C

4: 3.02 g / tetrahydrofuran / 3 h / 20 °C

5: 78 percent / BuLi / hexane; tetrahydrofuran / 4 h / -78 °C

6: Li; EtNH₂ / tetrahydrofuran / 2 h / -78 °C

7: 309 mg / 4-(dimethylamino)pyridine; Et₃N / CH₂Cl₂ / 6 h / 0 - 20 °C

8: N-bromosuccinimide / tetrahydrofuran; H₂O / 5 h / 0 °C

9: 137 mg / K₂CO₃; MeOH / 16 h

10: HIO₄*H₂O / H₂O; tetrahydrofuran / 3 h / 0 - 20 °C

11: pyridinium p-toluenesulfonate / CH₂Cl₂ / 8 h / 20 °C

12: 72 mg / NaBH₄ / methanol; diethyl ether / 16 h / 20 °C

13: Et₃N / CH₂Cl₂ / 2 h / 0 °C

14: 56 mg / dimethylsulfoxide / 18 h / 60 °C

15: 89 percent / DIBAL-H / toluene / 5 h / -78 °C

16: 95 percent / NaClO₂; KH₂PO₄; 2-methylbut-2-ene / H₂O; 2-methyl-propan-2-ol / 1 h

17: 65 percent / Bu₃P / CH₂Cl₂ / 0.5 h / -30 °C

18: 94 percent / TsOH*H₂O; aq. NaHCO₃ / methanol

With methanol; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium chlorite; sodium tetrahydroborate; potassium dihydrogenphosphate; N-Bromosuccinimide; n-butyllithium; 2-methyl-but-2-ene; tributylphosphine; pyridinium p-toluenesulfonate; lithium; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; ethylamine; periodic acid; triethylamine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; toluene; tert-butyl alcohol; 1: Alkylation / 2: Reduction / 3: Tosylation / 4: Substitution / 5: Alkylation / 6: Reduction / 7: Acetylation / 8: Epoxidation / 9: Deacetylation / 10: Hydrolysis / 11: Addition / 12: Reduction / 13: Condensation / 14: Substitution / 15: Reduction / 16: Oxidation / 17: Substitution / 18: Hydrolysis;

DOI:10.1002/1522-2675(20000906)83:9<2629::AID-HLCA2629>3.0.CO;2-W

Reference yield:

Geranylgeraniol (24034-73-9) → Se-phenyl (E,E,E,E,E,E,E)-31-hydroxy-5,9,13,17,21,25,29-heptmethylhentriaconta-5,9,13,17,21,25,29-heptaeneselenoate (229305-90-2)

Guidance literature:

Multi-step reaction with 20 steps

1: BuLi; 1,3-dimethyl-3,4,5,6-tetrahydropyrimidin-2(1H)-one / hexane; tetrahydrofuran / 3 h / 0 °C

2: 6.8 g / tetrahydrofuran / 3 h / 20 °C

3: 84 percent / BuLi / hexane; tetrahydrofuran / 4 h / -78 °C

4: Li; EtNH₂ / tetrahydrofuran / 2 h / -78 °C

5: BuLi; 1,3-dimethyl-3,4,5,6-tetrahydropyrimidin-2(1H)-one / hexane; tetrahydrofuran / 3 h / 0 °C

6: 3.02 g / tetrahydrofuran / 3 h / 20 °C

7: 78 percent / BuLi / hexane; tetrahydrofuran / 4 h / -78 °C

8: Li; EtNH₂ / tetrahydrofuran / 2 h / -78 °C

9: 309 mg / 4-(dimethylamino)pyridine; Et₃N / CH₂Cl₂ / 6 h / 0 - 20 °C

10: N-bromosuccinimide / tetrahydrofuran; H₂O / 5 h / 0 °C

11: 137 mg / K₂CO₃; MeOH / 16 h

12: HIO₄*H₂O / H₂O; tetrahydrofuran / 3 h / 0 - 20 °C

13: pyridinium p-toluenesulfonate / CH₂Cl₂ / 8 h / 20 °C

14: 72 mg / NaBH₄ / methanol; diethyl ether / 16 h / 20 °C

15: Et₃N / CH₂Cl₂ / 2 h / 0 °C

16: 56 mg / dimethylsulfoxide / 18 h / 60 °C

17: 89 percent / DIBAL-H / toluene / 5 h / -78 °C

18: 95 percent / NaClO₂; KH₂PO₄; 2-methylbut-2-ene / H₂O; 2-methyl-propan-2-ol / 1 h

19: 65 percent / Bu₃P / CH₂Cl₂ / 0.5 h / -30 °C

20: 94 percent / TsOH*H₂O; aq. NaHCO₃ / methanol

With methanol; dmap; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; sodium chlorite; sodium tetrahydroborate; potassium dihydrogenphosphate; N-Bromosuccinimide; n-butyllithium; 2-methyl-but-2-ene; tributylphosphine; pyridinium p-toluenesulfonate; lithium; diisobutylaluminium hydride; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; ethylamine; periodic acid; triethylamine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; toluene; tert-butyl alcohol; 1: Tosylation / 2: Substitution / 3: Alkylation / 4: Reduction / 5: Tosylation / 6: Substitution / 7: Alkylation / 8: Reduction / 9: Acetylation / 10: Epoxidation / 11: Deacetylation / 12: Hydrolysis / 13: Addition / 14: Reduction / 15: Condensation / 16: Substitution / 17: Reduction / 18: Oxidation / 19: Substitution / 20: Hydrolysis;

DOI:10.1002/1522-2675(20000906)83:9<2629::AID-HLCA2629>3.0.CO;2-W

upstream raw materials:

Se-phenyl (E,E,E,E,E,E,E)-5,9,13,17,21,25,29-heptamethyl-31-[(tetrahydro-2H-pyran-2-yl)oxy]hentriaconta-5,9,13,17,21,25,29-heptaeneselenoate

Geranylgeraniol

((2E,6E)-8-Bromo-3,7-dimethyl-octa-2,6-dienyloxymethyl)-benzene

[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenyl](phenyl)sulfane

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