(9S,10E,12R,13S,15Z)-12-t-butyldimethylsilyloxy-9-hydroxy-13-p-methoxybenzyloxyoctadeca-10,15-dienoic acid

Base Information

• Chemical Name: (9S,10E,12R,13S,15Z)-12-t-butyldimethylsilyloxy-9-hydroxy-13-p-methoxybenzyloxyoctadeca-10,15-dienoic acid
• CAS No.: 326921-60-2
• Molecular Formula: C₃₂H₅₄O₆Si
• Molecular Weight: 562.863

Synonyms:(9S,10E,12R,13S,15Z)-12-t-butyldimethylsilyloxy-9-hydroxy-13-p-methoxybenzyloxyoctadeca-10,15-dienoic acid

Chemical Property of (9S,10E,12R,13S,15Z)-12-t-butyldimethylsilyloxy-9-hydroxy-13-p-methoxybenzyloxyoctadeca-10,15-dienoic acid

Chemical Property:

Purity/Quality:

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MSDS Files:

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Technology Process of (9S,10E,12R,13S,15Z)-12-t-butyldimethylsilyloxy-9-hydroxy-13-p-methoxybenzyloxyoctadeca-10,15-dienoic acid

There total 12 articles about (9S,10E,12R,13S,15Z)-12-t-butyldimethylsilyloxy-9-hydroxy-13-p-methoxybenzyloxyoctadeca-10,15-dienoic 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%

methyl (9S,10E,12R,13S,15Z)-12-t-butyldimethylsilyloxy-9-hydroxy-13-p-methoxybenzyloxyoctadeca-10,15-dienoate (345994-22-1) → (9S,10E,12R,13S,15Z)-12-t-butyldimethylsilyloxy-9-hydroxy-13-p-methoxybenzyloxyoctadeca-10,15-dienoic acid (326921-60-2)

Guidance literature:

With lithium hydroxide; In methanol;

DOI:10.1016/S0040-4039(00)01285-5

Reference yield:

1-(2,2-dimethyl-[1,3]dioxolan-4-yl)-3,3-bis-ethylsulfanyl-propan-1-ol (67320-20-1,83692-41-5,94292-91-8,64722-95-8) → (9S,10E,12R,13S,15Z)-12-t-butyldimethylsilyloxy-9-hydroxy-13-p-methoxybenzyloxyoctadeca-10,15-dienoic acid (326921-60-2)

Guidance literature:

Multi-step reaction with 11 steps

1: 100 percent / sodium hydride / dimethylformamide; various solvent(s) / 2 h

2: 85 percent / HgCl₂; yellow HgO / acetonitrile; H₂O / 0.67 h / 0 °C

3: diethyl ether; tetrahydrofuran / 1 h / -78 °C

4: 96 percent / trifluoroacetic acid / tetrahydrofuran; H₂O / 30 h / 40 °C

5: 93 percent / pyridine / 1 h

6: 98 percent / imidazole / dimethylformamide / 15 h / 20 °C

7: 93 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 1 h / -50 - -10 °C

8: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.33 h

9: 93 percent / lithium chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1.5 h

10: 65 percent / (R)-CBS reagent; BH₃*THF / tetrahydrofuran; toluene / 1.5 h

11: 91 percent / LiOH*H₂O / methanol / 12 h / 20 °C

With pyridine; 1H-imidazole; lithium hydroxide; borane-THF; (R)-CBS reagent; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; lithium chloride; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 3: Wittig reaction / 9: Horner-Wadsworth-Emmons reaction;

DOI:10.1016/S0040-4020(01)00279-4

Reference yield:

p-methoxybenzyl chloride (824-94-2) → (9S,10E,12R,13S,15Z)-12-t-butyldimethylsilyloxy-9-hydroxy-13-p-methoxybenzyloxyoctadeca-10,15-dienoic acid (326921-60-2)

Guidance literature:

Multi-step reaction with 11 steps

1: 100 percent / sodium hydride / dimethylformamide; various solvent(s) / 2 h

2: 85 percent / HgCl₂; yellow HgO / acetonitrile; H₂O / 0.67 h / 0 °C

3: diethyl ether; tetrahydrofuran / 1 h / -78 °C

4: 96 percent / trifluoroacetic acid / tetrahydrofuran; H₂O / 30 h / 40 °C

5: 93 percent / pyridine / 1 h

6: 98 percent / imidazole / dimethylformamide / 15 h / 20 °C

7: 93 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 1 h / -50 - -10 °C

8: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.33 h

9: 93 percent / lithium chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 1.5 h

10: 65 percent / (R)-CBS reagent; BH₃*THF / tetrahydrofuran; toluene / 1.5 h

11: 91 percent / LiOH*H₂O / methanol / 12 h / 20 °C

With pyridine; 1H-imidazole; lithium hydroxide; borane-THF; (R)-CBS reagent; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; lithium chloride; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 3: Wittig reaction / 9: Horner-Wadsworth-Emmons reaction;

DOI:10.1016/S0040-4020(01)00279-4

upstream raw materials:

methyl (9S,10E,12R,13S,15Z)-12-t-butyldimethylsilyloxy-9-hydroxy-13-p-methoxybenzyloxyoctadeca-10,15-dienoate

1-(2,2-dimethyl-[1,3]dioxolan-4-yl)-3,3-bis-ethylsulfanyl-propan-1-ol

p-methoxybenzyl chloride

2-deoxy-3-O-<(4-methoxyphenyl)methyl>-4,5-O-(1-methylethylidene)-D-erythro-pentose

Downstream raw materials:

(9S,10E,12R,13S,15Z)-13-t-butyldiphenylsilyloxy-12-hydroxyoctadeca-10,15-dien-9-olide

(9S,10E,12R,13S,15Z)-12-t-butyldimethylsilyloxy-13-t-butyldiphenylsilyloxyoctadeca-10,15-dien-9-olide

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