(S,2E,4E)-8-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-4-methylocta-2,4-dien-1-amine

Base Information

Chemical Name:(S,2E,4E)-8-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-4-methylocta-2,4-dien-1-amine
CAS No.:175551-71-0
Molecular Formula:C₃₁H₄₉NO₂Si₂
Molecular Weight:523.907
Hs Code.:

Synonyms:(S,2E,4E)-8-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-4-methylocta-2,4-dien-1-amine

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Chemical Property of (S,2E,4E)-8-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-4-methylocta-2,4-dien-1-amine

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Technology Process of (S,2E,4E)-8-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-4-methylocta-2,4-dien-1-amine

There total 36 articles about (S,2E,4E)-8-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-4-methylocta-2,4-dien-1-amine 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: 96.0%

: 175551-70-9
(S,2E,4E)-8-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-4-methylocta-2,4-dienenitrile

: 175551-71-0
(S,2E,4E)-8-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-4-methylocta-2,4-dien-1-amine

Guidance literature:: With aluminium hydride; In tetrahydrofuran; at 0 ℃; for 5h;
DOI:10.1016/S0040-4039(98)00500-0

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 175551-71-0
(S,2E,4E)-8-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-4-methylocta-2,4-dien-1-amine

Guidance literature:: Multi-step reaction with 14 steps

1: 99 percent / NaH / tetrahydrofuran / 0.75 h / 20 °C

2: 99 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 3 h / -78 °C

3: 65 percent / CH₂Cl₂ / 3 h / Heating

4: K₃Fe(CN)6; K₂CO₃; MeSO₂NH₂ / OsO₄; (DHQ)2PHAL / 2-methyl-propan-2-ol / 5 h / 0 °C

5: pyridine / CH₂Cl₂ / cooling

6: potassium tert-butoxide / tetrahydrofuran / 0.42 h / -40 °C

7: LiOH / tetrahydrofuran; H₂O / 3 h / 45 °C

8: camphorsulfonic acid / CH₂Cl₂; acetone / 0.42 h

9: DIBAL / tetrahydrofuran / 0.17 h / -78 °C

10: triphenylphosphine; imidazole; I₂ / acetonitrile / 0.03 h

11: acetonitrile / 3.5 h / Heating

12: 30 mg / K₂CO₃ / methanol / 3.5 h / 20 °C

13: 89 percent / imidazole / CH₂Cl₂ / 1 h / 0 °C

14: 70 percent / AlH₃ / tetrahydrofuran / 1 h / 0 °C

With pyridine; 1H-imidazole; aluminium hydride; lithium hydroxide; oxalyl dichloride; methanesulfonamide; camphor-10-sulfonic acid; potassium tert-butylate; iodine; sodium hydride; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; potassium hexacyanoferrate(III); osmium(VIII) oxide; Hydroquinone 1,4-phthalazinediyl diether; In tetrahydrofuran; methanol; dichloromethane; water; acetone; acetonitrile; tert-butyl alcohol; 2: Swern oxidation / 3: Wittig reaction / 4: Sharpless dihydroxylation / 6: Horner-Emmons olefination;
DOI:10.1021/ol071145e

Reference yield:

: 73842-99-6
3-tert-butyldimethylsilyloxy-1-propanol

: 175551-71-0
(S,2E,4E)-8-(tert-butyldimethylsilyloxy)-6-(tert-butyldiphenylsilyloxy)-4-methylocta-2,4-dien-1-amine

Guidance literature:: Multi-step reaction with 13 steps

1: 99 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 3 h / -78 °C

2: 65 percent / CH₂Cl₂ / 3 h / Heating

3: K₃Fe(CN)6; K₂CO₃; MeSO₂NH₂ / OsO₄; (DHQ)2PHAL / 2-methyl-propan-2-ol / 5 h / 0 °C

4: pyridine / CH₂Cl₂ / cooling

5: potassium tert-butoxide / tetrahydrofuran / 0.42 h / -40 °C

6: LiOH / tetrahydrofuran; H₂O / 3 h / 45 °C

7: camphorsulfonic acid / CH₂Cl₂; acetone / 0.42 h

8: DIBAL / tetrahydrofuran / 0.17 h / -78 °C

9: triphenylphosphine; imidazole; I₂ / acetonitrile / 0.03 h

10: acetonitrile / 3.5 h / Heating

11: 30 mg / K₂CO₃ / methanol / 3.5 h / 20 °C

12: 89 percent / imidazole / CH₂Cl₂ / 1 h / 0 °C

13: 70 percent / AlH₃ / tetrahydrofuran / 1 h / 0 °C

With pyridine; 1H-imidazole; aluminium hydride; lithium hydroxide; oxalyl dichloride; methanesulfonamide; camphor-10-sulfonic acid; potassium tert-butylate; iodine; diisobutylaluminium hydride; potassium carbonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; potassium hexacyanoferrate(III); osmium(VIII) oxide; Hydroquinone 1,4-phthalazinediyl diether; In tetrahydrofuran; methanol; dichloromethane; water; acetone; acetonitrile; tert-butyl alcohol; 1: Swern oxidation / 2: Wittig reaction / 3: Sharpless dihydroxylation / 5: Horner-Emmons olefination;
DOI:10.1021/ol071145e