(5E,9E)-(3R,4S)-4-Benzyloxymethoxy-3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-6,10-dimethyl-14-oxo-pentadeca-5,9-dienal

Base Information

• Chemical Name: (5E,9E)-(3R,4S)-4-Benzyloxymethoxy-3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-6,10-dimethyl-14-oxo-pentadeca-5,9-dienal
• CAS No.: 128322-27-0
• Molecular Formula: C₃₃H₅₄O₅Si
• Molecular Weight: 558.874

Synonyms:(5E,9E)-(3R,4S)-4-Benzyloxymethoxy-3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-6,10-dimethyl-14-oxo-pentadeca-5,9-dienal

Chemical Property of (5E,9E)-(3R,4S)-4-Benzyloxymethoxy-3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-6,10-dimethyl-14-oxo-pentadeca-5,9-dienal

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (5E,9E)-(3R,4S)-4-Benzyloxymethoxy-3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-6,10-dimethyl-14-oxo-pentadeca-5,9-dienal

There total 21 articles about (5E,9E)-(3R,4S)-4-Benzyloxymethoxy-3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-6,10-dimethyl-14-oxo-pentadeca-5,9-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: 80.0%

(6E,10E)-(12S,13S)-12-Benzyloxymethoxy-15-(tert-butyl-dimethyl-silanyloxy)-13-(2-hydroxy-ethyl)-6,10-dimethyl-pentadeca-6,10-dien-2-one (128322-26-9) → (5E,9E)-(3R,4S)-4-Benzyloxymethoxy-3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-6,10-dimethyl-14-oxo-pentadeca-5,9-dienal (128322-27-0)

Guidance literature:

With dipyridinium dichromate; 4 A molecular sieve; In dichloromethane; for 2h; Ambient temperature;

DOI:10.1248/cpb.40.1742

Reference yield:

(5S)-5-(hydroxymethyl)-5H-furan-2-one (78508-96-0) → (5E,9E)-(3R,4S)-4-Benzyloxymethoxy-3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-6,10-dimethyl-14-oxo-pentadeca-5,9-dienal (128322-27-0)

Guidance literature:

Multi-step reaction with 21 steps

1: 95 percent / CSA / tetrahydrofuran / 15 h / 10 °C

2: 1.) LDA / 1.) hexane, THF, -78 deg C, 40 min, 2.) hexane, THF, -78 deg C, 30 min

3: 53 percent / diisobutylaluminum hydride (DIBAH) / hexane; tetrahydrofuran / 0.5 h

4: 66 percent / NaBH₄ / methanol / 0.33 h / 0 °C

5: 88 percent / imidazole / tetrahydrofuran / 20 h / Ambient temperature

6: 100 percent / diisopropylethylamine / 1,2-dichloro-ethane / 5 h / 60 °C

7: LAH / diethyl ether / 0.5 h / 0 °C

8: NaH / tetrahydrofuran; dimethylformamide / 5 h / Ambient temperature

9: MgBr / diethyl ether / 7 h / Ambient temperature

10: 99 percent / DMSO, oxalyl chloride, Et₃N / CH₂Cl₂ / 0.33 h / -70 °C

11: 85 percent / tetrahydrofuran / 1 h

12: 66 percent / Hg(II) acetate / 48 h / 135 °C

13: 76 percent / tetrahydrofuran / 1 h

14: Hg(II) acetate / 48 h / 135 °C

15: 99 percent / NaBH₄ / methanol / 0.5 h / 0 °C

16: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

17: NaI / acetone / 20 h / Ambient temperature

18: 1.) t-BuLi, 2.) HMPA / 1.) pentane, THF, from -78 deg C to 0 deg C, 2.) pentane, THF

19: AcOH / H₂O / 2 h / Ambient temperature

20: 89 percent / DDQ / CH₂Cl₂; H₂O / 1.5 h / Ambient temperature

21: 80 percent / powdered molecular sieves 4 A, pyridinium dichromate (PDC) / CH₂Cl₂ / 2 h / Ambient temperature

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; lithium aluminium tetrahydride; dipyridinium dichromate; oxalyl dichloride; 4 A molecular sieve; camphor-10-sulfonic acid; mercury(II) diacetate; tert.-butyl lithium; sodium hydride; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide; magnesium bromide; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone;

DOI:10.1248/cpb.40.1742

Reference yield:

tert-butyl (3R,4S)-3-(2-hydroxy)ethyl-4-hydroxy-5-tetrahydropyranyloxypentanoate (128322-02-1) → (5E,9E)-(3R,4S)-4-Benzyloxymethoxy-3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-6,10-dimethyl-14-oxo-pentadeca-5,9-dienal (128322-27-0)

Guidance literature:

Multi-step reaction with 17 steps

1: 88 percent / imidazole / tetrahydrofuran / 20 h / Ambient temperature

2: 100 percent / diisopropylethylamine / 1,2-dichloro-ethane / 5 h / 60 °C

3: LAH / diethyl ether / 0.5 h / 0 °C

4: NaH / tetrahydrofuran; dimethylformamide / 5 h / Ambient temperature

5: MgBr / diethyl ether / 7 h / Ambient temperature

6: 99 percent / DMSO, oxalyl chloride, Et₃N / CH₂Cl₂ / 0.33 h / -70 °C

7: 85 percent / tetrahydrofuran / 1 h

8: 66 percent / Hg(II) acetate / 48 h / 135 °C

9: 76 percent / tetrahydrofuran / 1 h

10: Hg(II) acetate / 48 h / 135 °C

11: 99 percent / NaBH₄ / methanol / 0.5 h / 0 °C

12: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

13: NaI / acetone / 20 h / Ambient temperature

14: 1.) t-BuLi, 2.) HMPA / 1.) pentane, THF, from -78 deg C to 0 deg C, 2.) pentane, THF

15: AcOH / H₂O / 2 h / Ambient temperature

16: 89 percent / DDQ / CH₂Cl₂; H₂O / 1.5 h / Ambient temperature

17: 80 percent / powdered molecular sieves 4 A, pyridinium dichromate (PDC) / CH₂Cl₂ / 2 h / Ambient temperature

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; lithium aluminium tetrahydride; dipyridinium dichromate; oxalyl dichloride; 4 A molecular sieve; mercury(II) diacetate; tert.-butyl lithium; sodium hydride; acetic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium iodide; magnesium bromide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone;

DOI:10.1248/cpb.40.1742

upstream raw materials:

(6E,10E)-(12S,13S)-12-Benzyloxymethoxy-15-(tert-butyl-dimethyl-silanyloxy)-13-(2-hydroxy-ethyl)-6,10-dimethyl-pentadeca-6,10-dien-2-one

(5S)-5-(hydroxymethyl)-5H-furan-2-one

(4S)-4-hydroxy-5-tetrahydropyranyloxy-2-pentenoic acid γ-lactone

tert-butyl (3R,4S)-3-(2-hydroxy)ethyl-4-hydroxy-5-tetrahydropyranyloxypentanoate

Downstream raw materials:

(3R,4S,5E,9E)-4-benzyloxymethyloxy-3-(2-tert-butyldimethylsilyloxyethyl)-6,10-dimethyl-14-oxo-5,9-pentadecadienoic acid

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