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

Base Information

• Chemical Name: (3R,4S,5E,9E)-4-benzyloxymethyloxy-3-(2-tert-butyldimethylsilyloxyethyl)-6,10-dimethyl-14-oxo-5,9-pentadecadienoic acid
• CAS No.: 128322-10-1
• Molecular Formula: C₃₃H₅₄O₆Si
• Molecular Weight: 574.874

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 25 articles about (3R,4S,5E,9E)-4-benzyloxymethyloxy-3-(2-tert-butyldimethylsilyloxyethyl)-6,10-dimethyl-14-oxo-5,9-pentadecadienoic acid 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: 100.0%

(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) → (3R,4S,5E,9E)-4-benzyloxymethyloxy-3-(2-tert-butyldimethylsilyloxyethyl)-6,10-dimethyl-14-oxo-5,9-pentadecadienoic acid (128322-10-1)

Guidance literature:

With sodium dihydrogen phosphate; 2-methyl-but-2-ene; sodium chloride; In tert-butyl alcohol; for 0.5h; Ambient temperature;

DOI:10.1248/cpb.40.1742

Reference yield:

(5S)-5-(hydroxymethyl)-5H-furan-2-one (78508-96-0) → (3R,4S,5E,9E)-4-benzyloxymethyloxy-3-(2-tert-butyldimethylsilyloxyethyl)-6,10-dimethyl-14-oxo-5,9-pentadecadienoic acid (128322-10-1)

Guidance literature:

Multi-step reaction with 22 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

22: 100 percent / 2-methyl-2-butene, aq. NaCl, sodium dihydrogen phosphate / 2-methyl-propan-2-ol / 0.5 h / Ambient temperature

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; lithium aluminium tetrahydride; dipyridinium dichromate; sodium dihydrogen phosphate; 2-methyl-but-2-ene; 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; sodium chloride; magnesium bromide; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;

DOI:10.1248/cpb.40.1742

Reference yield:

(4S)-4-hydroxy-5-tetrahydropyranyloxy-2-pentenoic acid γ-lactone (128387-70-2) → (3R,4S,5E,9E)-4-benzyloxymethyloxy-3-(2-tert-butyldimethylsilyloxyethyl)-6,10-dimethyl-14-oxo-5,9-pentadecadienoic acid (128322-10-1)

Guidance literature:

Multi-step reaction with 21 steps

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

2: 53 percent / diisobutylaluminum hydride (DIBAH) / hexane; tetrahydrofuran / 0.5 h

3: 66 percent / NaBH₄ / methanol / 0.33 h / 0 °C

4: 88 percent / imidazole / tetrahydrofuran / 20 h / Ambient temperature

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

6: LAH / diethyl ether / 0.5 h / 0 °C

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

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

9: 99 percent / DMSO, oxalyl chloride, Et₃N / CH₂Cl₂ / 0.33 h / -70 °C

10: 85 percent / tetrahydrofuran / 1 h

11: 66 percent / Hg(II) acetate / 48 h / 135 °C

12: 76 percent / tetrahydrofuran / 1 h

13: Hg(II) acetate / 48 h / 135 °C

14: 99 percent / NaBH₄ / methanol / 0.5 h / 0 °C

15: Et₃N / CH₂Cl₂ / 0.5 h / 0 °C

16: NaI / acetone / 20 h / Ambient temperature

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

18: AcOH / H₂O / 2 h / Ambient temperature

19: 89 percent / DDQ / CH₂Cl₂; H₂O / 1.5 h / Ambient temperature

20: 80 percent / powdered molecular sieves 4 A, pyridinium dichromate (PDC) / CH₂Cl₂ / 2 h / Ambient temperature

21: 100 percent / 2-methyl-2-butene, aq. NaCl, sodium dihydrogen phosphate / 2-methyl-propan-2-ol / 0.5 h / Ambient temperature

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; lithium aluminium tetrahydride; dipyridinium dichromate; sodium dihydrogen phosphate; 2-methyl-but-2-ene; oxalyl dichloride; 4 A molecular sieve; 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; sodium chloride; magnesium bromide; lithium diisopropyl amide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; tert-butyl alcohol;

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

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

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

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

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