(10E,16E)-(3R,4R,5R,6R,9S,13R,15R,19S,20R,21S,22S)-5-(tert-Butyl-dimethyl-silanyloxy)-9,15-dimethoxy-4,6,13,20,22-pentamethyl-3-methylsulfanylmethoxy-19,21-bis-triethylsilanyloxy-23-trityloxy-tricosa-10,16-dienal

Base Information

• Chemical Name: (10E,16E)-(3R,4R,5R,6R,9S,13R,15R,19S,20R,21S,22S)-5-(tert-Butyl-dimethyl-silanyloxy)-9,15-dimethoxy-4,6,13,20,22-pentamethyl-3-methylsulfanylmethoxy-19,21-bis-triethylsilanyloxy-23-trityloxy-tricosa-10,16-dienal
• CAS No.: 423772-14-9
• Molecular Formula: C₆₉H₁₁₆O₈SSi₃
• Molecular Weight: 1190

Synonyms:(10E,16E)-(3R,4R,5R,6R,9S,13R,15R,19S,20R,21S,22S)-5-(tert-Butyl-dimethyl-silanyloxy)-9,15-dimethoxy-4,6,13,20,22-pentamethyl-3-methylsulfanylmethoxy-19,21-bis-triethylsilanyloxy-23-trityloxy-tricosa-10,16-dienal

Chemical Property of (10E,16E)-(3R,4R,5R,6R,9S,13R,15R,19S,20R,21S,22S)-5-(tert-Butyl-dimethyl-silanyloxy)-9,15-dimethoxy-4,6,13,20,22-pentamethyl-3-methylsulfanylmethoxy-19,21-bis-triethylsilanyloxy-23-trityloxy-tricosa-10,16-dienal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

Technology Process of (10E,16E)-(3R,4R,5R,6R,9S,13R,15R,19S,20R,21S,22S)-5-(tert-Butyl-dimethyl-silanyloxy)-9,15-dimethoxy-4,6,13,20,22-pentamethyl-3-methylsulfanylmethoxy-19,21-bis-triethylsilanyloxy-23-trityloxy-tricosa-10,16-dienal

There total 21 articles about (10E,16E)-(3R,4R,5R,6R,9S,13R,15R,19S,20R,21S,22S)-5-(tert-Butyl-dimethyl-silanyloxy)-9,15-dimethoxy-4,6,13,20,22-pentamethyl-3-methylsulfanylmethoxy-19,21-bis-triethylsilanyloxy-23-trityloxy-tricosa-10,16-dienal 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: 83.0%

(10E,16E)-(3R,4R,5R,6R,9S,13R,15R,19S,20R,21S,22S)-5-(tert-Butyl-dimethyl-silanyloxy)-9,15-dimethoxy-4,6,13,20,22-pentamethyl-3-methylsulfanylmethoxy-19,21-bis-triethylsilanyloxy-23-trityloxy-tricosa-10,16-dien-1-ol (423772-13-8) → (10E,16E)-(3R,4R,5R,6R,9S,13R,15R,19S,20R,21S,22S)-5-(tert-Butyl-dimethyl-silanyloxy)-9,15-dimethoxy-4,6,13,20,22-pentamethyl-3-methylsulfanylmethoxy-19,21-bis-triethylsilanyloxy-23-trityloxy-tricosa-10,16-dienal (423772-14-9)

Guidance literature:

With C₆H₄(COO)I(OAc)3; In dichloromethane; at 20 ℃; for 0.25h;

DOI:10.1016/S0040-4020(01)01206-6

Reference yield:

(S)-2-methyl-1-(triisopropylsilyloxy)pentan-3-one (158783-76-7) → (10E,16E)-(3R,4R,5R,6R,9S,13R,15R,19S,20R,21S,22S)-5-(tert-Butyl-dimethyl-silanyloxy)-9,15-dimethoxy-4,6,13,20,22-pentamethyl-3-methylsulfanylmethoxy-19,21-bis-triethylsilanyloxy-23-trityloxy-tricosa-10,16-dienal (423772-14-9)

Guidance literature:

Multi-step reaction with 13 steps

1: 83 percent / Sn(OTf)2; Et₃N / CH₂Cl₂ / -78 - -20 °C

2: 80 percent / Me₄NBH(OAc)3 / acetonitrile; acetic acid / 25 h / -20 °C

3: 100 percent / hydrogen / 20 percent Pd(OH)2/C / dioxane / 15 h / 20 °C

4: 93 percent / PBu₃ / dimethylformamide / 1.5 h / 20 °C

5: 100 percent / Bu₄NF / tetrahydrofuran / 3 h / 20 °C

6: 96 percent / pyridine / 11.5 h / 50 °C

7: 93 percent / imidazole / dimethylformamide / 1.5 h / 50 °C

8: 98 percent / m-chloroperbenzoic acid; NaHCO₃ / CH₂Cl₂ / 1.5 h / 20 °C

9: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

10: DMAP / pyridine / 3.5 h / 20 °C

11: 5 percent Na-Hg; NaH₂PO₄ / methanol / 35 h / 0 °C

12: 96 percent / DIBAL / CH₂Cl₂; hexane / 1 h / -78 °C

13: 83 percent / C₆H₄(COO)I(OAc)3 / CH₂Cl₂ / 0.25 h / 20 °C

With pyridine; 1H-imidazole; dmap; sodium dihydrogenphosphate; tin(II) trifluoromethanesulfonate; n-butyllithium; sodium amalgam; tributylphosphine; C₆H₄(COO)I(OAc)3; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; sodium hydrogencarbonate; triethylamine; 3-chloro-benzenecarboperoxoic acid; tetramethylammonium triacetoxyborohydride; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; hexane; dichloromethane; acetic acid; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4020(01)01206-6

Reference yield:

(2S,3S,4R,5S)-7-Benzyloxy-2,4-dimethyl-1-triisopropylsilanyloxy-heptane-3,5-diol (423772-05-8) → (10E,16E)-(3R,4R,5R,6R,9S,13R,15R,19S,20R,21S,22S)-5-(tert-Butyl-dimethyl-silanyloxy)-9,15-dimethoxy-4,6,13,20,22-pentamethyl-3-methylsulfanylmethoxy-19,21-bis-triethylsilanyloxy-23-trityloxy-tricosa-10,16-dienal (423772-14-9)

Guidance literature:

Multi-step reaction with 11 steps

1: 100 percent / hydrogen / 20 percent Pd(OH)2/C / dioxane / 15 h / 20 °C

2: 93 percent / PBu₃ / dimethylformamide / 1.5 h / 20 °C

3: 100 percent / Bu₄NF / tetrahydrofuran / 3 h / 20 °C

4: 96 percent / pyridine / 11.5 h / 50 °C

5: 93 percent / imidazole / dimethylformamide / 1.5 h / 50 °C

6: 98 percent / m-chloroperbenzoic acid; NaHCO₃ / CH₂Cl₂ / 1.5 h / 20 °C

7: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

8: DMAP / pyridine / 3.5 h / 20 °C

9: 5 percent Na-Hg; NaH₂PO₄ / methanol / 35 h / 0 °C

10: 96 percent / DIBAL / CH₂Cl₂; hexane / 1 h / -78 °C

11: 83 percent / C₆H₄(COO)I(OAc)3 / CH₂Cl₂ / 0.25 h / 20 °C

With pyridine; 1H-imidazole; dmap; sodium dihydrogenphosphate; n-butyllithium; sodium amalgam; tributylphosphine; C₆H₄(COO)I(OAc)3; tetrabutyl ammonium fluoride; hydrogen; diisobutylaluminium hydride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)01206-6

upstream raw materials:

(10E,16E)-(3R,4R,5R,6R,9S,13R,15R,19S,20R,21S,22S)-5-(tert-Butyl-dimethyl-silanyloxy)-9,15-dimethoxy-4,6,13,20,22-pentamethyl-3-methylsulfanylmethoxy-19,21-bis-triethylsilanyloxy-23-trityloxy-tricosa-10,16-dien-1-ol

(S)-2-methyl-1-(triisopropylsilyloxy)pentan-3-one

2,2-Dimethyl-propionic acid (3R,4R,5R,6R,9S)-5-(tert-butyl-dimethyl-silanyloxy)-9-methoxy-4,6-dimethyl-10-oxo-3-triethylsilanyloxy-decyl ester

C₃₃H₃₆O₄S

Downstream raw materials:

(2E,4E,14E,20E)-(7R,8R,9R,10R,13S,17R,19R,23S,24R,25S,26S)-9-(tert-Butyl-dimethyl-silanyloxy)-13,19-dimethoxy-8,10,17,24,26-pentamethyl-7-methylsulfanylmethoxy-23,25-bis-triethylsilanyloxy-27-trityloxy-heptacosa-2,4,14,20-tetraenoic acid ethyl ester

(2E,4E,14E,20E)-(7R,8R,9R,10R,13S,17R,19R,23S,24R,25S,26S)-9-(tert-Butyl-dimethyl-silanyloxy)-23,25-dihydroxy-13,19-dimethoxy-8,10,17,24,26-pentamethyl-7-methylsulfanylmethoxy-27-trityloxy-heptacosa-2,4,14,20-tetraenoic acid ethyl ester

C₇₁H₁₁₁NO₁₀Si₂

(3E,5E,15E,21E)-(8R,9R,10R,11R,14S,18R,20R,24S)-10-(tert-Butyl-dimethyl-silanyloxy)-24-((1S,2S,3S)-2-hydroxy-1,3-dimethyl-4-trityloxy-butyl)-14,20-dimethoxy-9,11,18-trimethyl-8-methylsulfanylmethoxy-oxacyclotetracosa-3,5,15,21-tetraen-2-one

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