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

Base Information

• Chemical Name: (9R,10E,12R,13S,15Z)-12-t-butyldimethylsilyloxy-13-p-methoxybenzyloxyoctadeca-10,15-dien-9-olide
• CAS No.: 326921-54-4
• Molecular Formula: C₃₂H₅₂O₅Si
• Molecular Weight: 544.847

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 14 articles about (9R,10E,12R,13S,15Z)-12-t-butyldimethylsilyloxy-13-p-methoxybenzyloxyoctadeca-10,15-dien-9-olide 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: 68.0%

(9R,10E,12R,13S,15Z)-12-t-butyldimethylsilyloxy-9-hydroxy-13-p-methoxybenzyloxyoctadeca-10,15-dienoic acid (345994-12-9) → (9R,10E,12R,13S,15Z)-12-t-butyldimethylsilyloxy-13-p-methoxybenzyloxyoctadeca-10,15-dien-9-olide (326921-54-4) + (10R,20R)-10,20-Bis-[(1E,6Z)-(3R,4S)-3-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-nona-1,6-dienyl]-1,11-dioxa-cycloicosane-2,12-dione

Guidance literature:

(9R,10E,12R,13S,15Z)-12-t-butyldimethylsilyloxy-9-hydroxy-13-p-methoxybenzyloxyoctadeca-10,15-dienoic acid; With 2,4,6-trichlorobenzoyl chloride; triethylamine; In tetrahydrofuran; at 20 ℃; for 1h;

With dmap; In tetrahydrofuran; toluene; Heating;

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

Reference yield: 68.0%

(9R,10E,12R,13S,15Z)-12-t-butyldimethylsilyloxy-9-hydroxy-13-p-methoxybenzyloxyoctadeca-10,15-dienoic acid (345994-12-9) → (9R,10E,12R,13S,15Z)-12-t-butyldimethylsilyloxy-13-p-methoxybenzyloxyoctadeca-10,15-dien-9-olide (326921-54-4)

Guidance literature:

(9R,10E,12R,13S,15Z)-12-t-butyldimethylsilyloxy-9-hydroxy-13-p-methoxybenzyloxyoctadeca-10,15-dienoic acid; With 2,4,6-trichlorobenzoyl chloride; triethylamine; In tetrahydrofuran;

With dmap; In toluene; for 12h; Heating;

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) → (9R,10E,12R,13S,15Z)-12-t-butyldimethylsilyloxy-13-p-methoxybenzyloxyoctadeca-10,15-dien-9-olide (326921-54-4)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 100 percent / NaH / dimethylformamide

2.1: 85 percent / HgCl₂; HgO / acetonitrile; H₂O

3.1: 68 percent / NaHMDS / diethyl ether / -78 °C

4.1: 96 percent / TFA / tetrahydrofuran; H₂O / 40 °C

5.1: 93 percent / pyridine

6.1: 98 percent / imidazole / dimethylformamide / 40 °C

7.1: 93 percent / DIBAL / CH₂Cl₂ / -50 - -10 °C

8.1: 96 percent / Dess-Martin periodinane / CH₂Cl₂

9.1: 93 percent / DBU; LiCl / acetonitrile

10.1: (R)-CBS reagent; BH₃*THF / tetrahydrofuran

11.1: 100 percent / LiOH / methanol

12.1: 2,4,6-trichlorobenzoyl chloride; NEt₃ / tetrahydrofuran

12.2: 68 percent / DMAP / toluene / 12 h / Heating

With 1H-imidazole; lithium hydroxide; borane-THF; (R)-CBS reagent; 2,4,6-trichlorobenzoyl chloride; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic acid; lithium chloride; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 3.1: Wittig reaction / 9.1: Horner-Wadsworth-Emmons reaction;

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

upstream raw materials:

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

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:

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

Methanesulfonic acid (Z)-(1R,2S)-2-(tert-butyl-diphenyl-silanyloxy)-1-[(E)-2-((R)-10-oxo-oxecan-2-yl)-vinyl]-hept-4-enyl ester

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

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