(E)-(2S,6R,8S)-8-(tert-Butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-non-4-enoic acid 4-methoxy-benzyl ester

Base Information

• Chemical Name: (E)-(2S,6R,8S)-8-(tert-Butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-non-4-enoic acid 4-methoxy-benzyl ester
• CAS No.: 156659-95-9
• Molecular Formula: C₂₆H₄₄O₄Si
• Molecular Weight: 448.718

Synonyms:(E)-(2S,6R,8S)-8-(tert-Butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-non-4-enoic acid 4-methoxy-benzyl ester

Chemical Property of (E)-(2S,6R,8S)-8-(tert-Butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-non-4-enoic acid 4-methoxy-benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(2S,6R,8S)-8-(tert-Butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-non-4-enoic acid 4-methoxy-benzyl ester

There total 10 articles about (E)-(2S,6R,8S)-8-(tert-Butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-non-4-enoic acid 4-methoxy-benzyl ester 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: 85.0%

(E)-(2S,6R,8S)-8-{[tert-butyl(dimethyl)silyl]oxy}-2,4,6-trimethylnon-4-enoic acid (117289-84-6) + 4-Methoxybenzyl alcohol (105-13-5) → (E)-(2S,6R,8S)-8-(tert-Butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-non-4-enoic acid 4-methoxy-benzyl ester (156659-95-9)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; for 9h; Ambient temperature;

DOI:10.1016/S0040-4039(00)75846-1

Reference yield:

(2S,4S)-pentane-2,4-diol (72345-23-4) → (E)-(2S,6R,8S)-8-(tert-Butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-non-4-enoic acid 4-methoxy-benzyl ester (156659-95-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 1) NaH (60percent in oil) / 1) THF, 2 h, RT, 2) THF, 45 min

2: 84 percent / pyridine / 72 h / 4 °C

3: 85 percent / hexamethylphosphoric acid triamide / 0 deg C, 30 min; RT, 24 h

4: 1) DIBAL-H (0.93 M in hexane), 2) H₂O, KHSO₄ / 1) CH₂Cl₂, -78 deg C, 1.5 h, 2) CH₂Cl₂, 78 deg C to RT

5: CH₂Cl₂ / 72 h / Ambient temperature

6: 89 percent / DIBAL-H (1.5 M in hexane) / CH₂Cl₂ / 0.5 h / -78 °C

7: PPh₃, I₂, imidazole / acetonitrile; tetrahydrofuran / 0.17 h / -10 °C

8: 1) 1.0 M sodium hexamethyldisilazide in THF / 1)THF, -78 deg C, 1 h, 2) THF, -72 deg C, 24 h

9: 96 percent / LiOH, 30percent H₂O₂ / tetrahydrofuran / 1 h / 0 °C

10: 85 percent / DCC, DMAP / CH₂Cl₂ / 0 deg C, 1 h; RT, 24 h

With pyridine; 1H-imidazole; dmap; lithium hydroxide; potassium hydrogensulfate; water; dihydrogen peroxide; iodine; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; dicyclohexyl-carbodiimide; triphenylphosphine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; acetonitrile;

DOI:10.3987/COM-97-S41

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (E)-(2S,6R,8S)-8-(tert-Butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-non-4-enoic acid 4-methoxy-benzyl ester (156659-95-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 1) NaH (60percent in oil) / 1) THF, 2 h, RT, 2) THF, 45 min

2: 84 percent / pyridine / 72 h / 4 °C

3: 85 percent / hexamethylphosphoric acid triamide / 0 deg C, 30 min; RT, 24 h

4: 1) DIBAL-H (0.93 M in hexane), 2) H₂O, KHSO₄ / 1) CH₂Cl₂, -78 deg C, 1.5 h, 2) CH₂Cl₂, 78 deg C to RT

5: CH₂Cl₂ / 72 h / Ambient temperature

6: 89 percent / DIBAL-H (1.5 M in hexane) / CH₂Cl₂ / 0.5 h / -78 °C

7: PPh₃, I₂, imidazole / acetonitrile; tetrahydrofuran / 0.17 h / -10 °C

8: 1) 1.0 M sodium hexamethyldisilazide in THF / 1)THF, -78 deg C, 1 h, 2) THF, -72 deg C, 24 h

9: 96 percent / LiOH, 30percent H₂O₂ / tetrahydrofuran / 1 h / 0 °C

10: 85 percent / DCC, DMAP / CH₂Cl₂ / 0 deg C, 1 h; RT, 24 h

With pyridine; 1H-imidazole; dmap; lithium hydroxide; potassium hydrogensulfate; water; dihydrogen peroxide; iodine; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; dicyclohexyl-carbodiimide; triphenylphosphine; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; acetonitrile;

DOI:10.3987/COM-97-S41

upstream raw materials:

(E)-(2S,6R,8S)-8-{[tert-butyl(dimethyl)silyl]oxy}-2,4,6-trimethylnon-4-enoic acid

4-Methoxybenzyl alcohol

(2R,4S)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-methylpentanal

(2S,4S)-pentane-2,4-diol

Downstream raw materials:

(E)-(2S,6R,8S)-8-Hydroxy-2,4,6-trimethyl-non-4-enoic acid 4-methoxy-benzyl ester

(E)-(2S,6R,8S)-8-((S)-2-{(R)-2-[((S)-2-tert-Butoxycarbonylamino-propionyl)-methyl-amino]-3-[4-(2,6-dichloro-benzyloxy)-3-iodo-phenyl]-propionylamino}-propionyloxy)-2,4,6-trimethyl-non-4-enoic acid 4-methoxy-benzyl ester

(E)-(2S,6R,8R)-8-Hydroxy-2,4,6-trimethyl-non-4-enoic acid 4-methoxy-benzyl ester

geodiamolide A

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