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

Base Information

• Chemical Name: methyl (9S,10E,12R,13S,15Z)-12-t-butyldimethylsilyloxy-9-hydroxy-13-p-methoxybenzyloxyoctadeca-10,15-dienoate
• CAS No.: 345994-22-1
• Molecular Formula: C₃₃H₅₆O₆Si
• Molecular Weight: 576.89

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

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

Chemical Property:

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

There total 12 articles about methyl (9S,10E,12R,13S,15Z)-12-t-butyldimethylsilyloxy-9-hydroxy-13-p-methoxybenzyloxyoctadeca-10,15-dienoate 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: 66.0%

methyl (10E,12R,13S,15Z)-12-t-butyldimethylsilyloxy-13-p-methoxybenzyloxy-9-oxooctadeca-10,15-dienoate (326921-52-2) → methyl (9R,10E,12R,13S,15Z)-12-t-butyldimethylsilyloxy-9-hydroxy-13-p-methoxybenzyloxyoctadeca-10,15-dienoate (326921-53-3) + methyl (9S,10E,12R,13S,15Z)-12-t-butyldimethylsilyloxy-9-hydroxy-13-p-methoxybenzyloxyoctadeca-10,15-dienoate (345994-22-1) + methyl (10Z,13S,15Z)-12-t-butyldimethylsilyloxy-9-hydroxy-13-p-methoxybenzyloxyoctadeca-10,15-dienoate + methyl (10E,12S,13S,15Z)-12-t-butyldimethylsilyloxy-9-hydroxy-13-p-methoxybenzyloxyoctadeca-10,15-dienoate

Guidance literature:

With borane-THF; (S)-CBS reagent; In tetrahydrofuran; toluene; for 1.5h;

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

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

Guidance literature:

Multi-step reaction with 10 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

With pyridine; 1H-imidazole; 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; 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) → methyl (9S,10E,12R,13S,15Z)-12-t-butyldimethylsilyloxy-9-hydroxy-13-p-methoxybenzyloxyoctadeca-10,15-dienoate (345994-22-1)

Guidance literature:

Multi-step reaction with 10 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

With pyridine; 1H-imidazole; 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; 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 (10E,12R,13S,15Z)-12-t-butyldimethylsilyloxy-13-p-methoxybenzyloxy-9-oxooctadeca-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)-12-t-butyldimethylsilyloxy-9-hydroxy-13-p-methoxybenzyloxyoctadeca-10,15-dienoic acid

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

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

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

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