(2E,4Z,6Z,8R,10R)-(tert-butyldiphenylsilyl)oxy-8-(tert-butyldimethylsilyl)oxy-10-formyl-10-(triethylsilyl)oxy-2,4,6-undecatriene

Base Information

• Chemical Name: (2E,4Z,6Z,8R,10R)-(tert-butyldiphenylsilyl)oxy-8-(tert-butyldimethylsilyl)oxy-10-formyl-10-(triethylsilyl)oxy-2,4,6-undecatriene
• CAS No.: 343982-05-8
• Molecular Formula: C₃₉H₆₂O₄Si₃
• Molecular Weight: 679.175
• Mol file: 343982-05-8.mol

Synonyms:(2E,4Z,6Z,8R,10R)-(tert-butyldiphenylsilyl)oxy-8-(tert-butyldimethylsilyl)oxy-10-formyl-10-(triethylsilyl)oxy-2,4,6-undecatriene

Chemical Property of (2E,4Z,6Z,8R,10R)-(tert-butyldiphenylsilyl)oxy-8-(tert-butyldimethylsilyl)oxy-10-formyl-10-(triethylsilyl)oxy-2,4,6-undecatriene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,4Z,6Z,8R,10R)-(tert-butyldiphenylsilyl)oxy-8-(tert-butyldimethylsilyl)oxy-10-formyl-10-(triethylsilyl)oxy-2,4,6-undecatriene

There total 16 articles about (2E,4Z,6Z,8R,10R)-(tert-butyldiphenylsilyl)oxy-8-(tert-butyldimethylsilyl)oxy-10-formyl-10-(triethylsilyl)oxy-2,4,6-undecatriene 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: 91.0%

(2E,4Z,6Z,8R,10R)-1-(tert-butyldiphenylsilyl)oxy-8-(tert-butyldimethylsilyl)oxy-11-hydroxy-10-(triethylsilyl)oxy-2,4,6-undecatriene (343982-04-7) → (2E,4Z,6Z,8R,10R)-(tert-butyldiphenylsilyl)oxy-8-(tert-butyldimethylsilyl)oxy-10-formyl-10-(triethylsilyl)oxy-2,4,6-undecatriene (343982-05-8)

Guidance literature:

With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; at 25 ℃; for 1h;

DOI:10.1021/ja010195q

Reference yield:

(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone (52813-63-5) → (2E,4Z,6Z,8R,10R)-(tert-butyldiphenylsilyl)oxy-8-(tert-butyldimethylsilyl)oxy-10-formyl-10-(triethylsilyl)oxy-2,4,6-undecatriene (343982-05-8)

Guidance literature:

Multi-step reaction with 16 steps

1.1: 95 percent / BF₃*OEt₂ / cyclohexane; CH₂Cl₂ / 25 °C

2.1: DIBAL-H / CH₂Cl₂; toluene / 1.5 h / -78 °C

3.1: 73 percent / MsCl; Et₃N; DMAP / CH₂Cl₂ / 2.5 h / Heating

4.1: (DHQD)2AQN; K₂OsO₂(OH)4; K₃Fe(CN)6 / K₂CO₃; MeSO₂NH₂ / 2-methyl-propan-2-ol; H₂O / 24 h / 2 °C

5.1: Et₃N / CH₂Cl₂ / 0.5 h / -78 °C

6.1: 88 percent / KHMDS; 18-crown-6/MeCN complex / tetrahydrofuran; toluene / 2 h / 0 °C

7.1: 95 percent / Et₃N / CH₂Cl₂ / 0.5 h / -30 °C

8.1: 90 percent / DIBAL-H / toluene; hexane / 0.33 h / -20 °C

9.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 25 °C

10.1: PPh₃ / CH₂Cl₂ / 0.08 h / 0 °C

10.2: 3.90 g / Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

11.1: 95 percent / DDQ / CH₂Cl₂; H₂O / 1.5 h / 25 °C

12.1: 93 percent / i-Pr₂NEt; DMAP / CH₂Cl₂ / 0.5 h / 25 °C

13.1: 84 percent / Bu₃SnH; (Ph₃P)4Pd / benzene / 2.5 h / 25 °C

14.1: 82 percent / iPr₂NEt; N-methylpyrrolidinone; (CH₃CN)2PdCl₂ / 25 °C

15.1: 98 percent / DIBAL-H / toluene / 0.08 h / -78 °C

16.1: 91 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 25 °C

With 1-methyl-pyrrolidin-2-one; dmap; dichloro bis(acetonitrile) palladium(II); tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium dioxotetrahydroxoosmate(VI); hydroquinidine anthraquinone-1,4-diyl diether; 18-crown-6 ether; boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; acetonitrile; 2,3-dicyano-5,6-dichloro-p-benzoquinone; potassium hexacyanoferrate(III); methanesulfonamide; potassium carbonate; In tetrahydrofuran; hexane; dichloromethane; cyclohexane; water; toluene; tert-butyl alcohol; benzene; 4.1: Sharpless assymetric dihydroxylation / 9.1: Dess-Martin oxidation / 10.1: Corey and Fuchs reaction / 14.1: Stille coupling / 16.1: Dess-Martin oxidation;

DOI:10.1021/ja010195q

Reference yield:

(4R)-4-[(4-methoxybenzyl)oxymethyl]-γ-butyrolactone (86771-48-4) → (2E,4Z,6Z,8R,10R)-(tert-butyldiphenylsilyl)oxy-8-(tert-butyldimethylsilyl)oxy-10-formyl-10-(triethylsilyl)oxy-2,4,6-undecatriene (343982-05-8)

Guidance literature:

Multi-step reaction with 15 steps

1.1: DIBAL-H / CH₂Cl₂; toluene / 1.5 h / -78 °C

2.1: 73 percent / MsCl; Et₃N; DMAP / CH₂Cl₂ / 2.5 h / Heating

3.1: (DHQD)2AQN; K₂OsO₂(OH)4; K₃Fe(CN)6 / K₂CO₃; MeSO₂NH₂ / 2-methyl-propan-2-ol; H₂O / 24 h / 2 °C

4.1: Et₃N / CH₂Cl₂ / 0.5 h / -78 °C

5.1: 88 percent / KHMDS; 18-crown-6/MeCN complex / tetrahydrofuran; toluene / 2 h / 0 °C

6.1: 95 percent / Et₃N / CH₂Cl₂ / 0.5 h / -30 °C

7.1: 90 percent / DIBAL-H / toluene; hexane / 0.33 h / -20 °C

8.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h / 25 °C

9.1: PPh₃ / CH₂Cl₂ / 0.08 h / 0 °C

9.2: 3.90 g / Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

10.1: 95 percent / DDQ / CH₂Cl₂; H₂O / 1.5 h / 25 °C

11.1: 93 percent / i-Pr₂NEt; DMAP / CH₂Cl₂ / 0.5 h / 25 °C

12.1: 84 percent / Bu₃SnH; (Ph₃P)4Pd / benzene / 2.5 h / 25 °C

13.1: 82 percent / iPr₂NEt; N-methylpyrrolidinone; (CH₃CN)2PdCl₂ / 25 °C

14.1: 98 percent / DIBAL-H / toluene / 0.08 h / -78 °C

15.1: 91 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 25 °C

With 1-methyl-pyrrolidin-2-one; dmap; dichloro bis(acetonitrile) palladium(II); tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium dioxotetrahydroxoosmate(VI); hydroquinidine anthraquinone-1,4-diyl diether; 18-crown-6 ether; tri-n-butyl-tin hydride; potassium hexamethylsilazane; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; acetonitrile; 2,3-dicyano-5,6-dichloro-p-benzoquinone; potassium hexacyanoferrate(III); methanesulfonamide; potassium carbonate; In tetrahydrofuran; hexane; dichloromethane; water; toluene; tert-butyl alcohol; benzene; 3.1: Sharpless assymetric dihydroxylation / 8.1: Dess-Martin oxidation / 9.1: Corey and Fuchs reaction / 13.1: Stille coupling / 15.1: Dess-Martin oxidation;

DOI:10.1021/ja010195q

upstream raw materials:

(2E,4Z,6Z,8R,10R)-1-(tert-butyldiphenylsilyl)oxy-8-(tert-butyldimethylsilyl)oxy-11-hydroxy-10-(triethylsilyl)oxy-2,4,6-undecatriene

(5R)-2,3,4,5-tetrahydro-5-hydroxymethyl-2-furanone

(4R)-4-[(4-methoxybenzyl)oxymethyl]-γ-butyrolactone

(R)-5-[(4-methoxybenzyl)oxy]methyl-4,5-dihydrofurane

Downstream raw materials:

[(6Z,8Z,10E)-(3R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-12-(tert-butyl-diphenyl-silanyloxy)-2-hydroxy-3-triethylsilanyloxy-dodeca-6,8,10-trienyl]-phosphonic acid diethyl ester

phosphoric acid 3-(tert-butyl-dimethyl-silanyloxy)-1-[1-(tert-butyl-dimethyl-silanyloxy)-1-methyl-3-(6-oxo-3,6-dihydro-2H-pyran-2-yl)-allyl]-10-(tert-butyl-diphenyl-silanyloxy)-deca-4,6,8-trienyl ester bis-(4-methoxy-benzyl) ester

[(6Z,8Z,10E)-(3R,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-12-(tert-butyl-diphenyl-silanyloxy)-2-oxo-3-triethylsilanyloxy-dodeca-6,8,10-trienyl]-phosphonic acid diethyl ester

(R)-6-[(1E,7Z,9Z,11E)-(3R,4R,6R)-3,6-Bis-(tert-butyl-dimethyl-silanyloxy)-13-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-3-methyl-trideca-1,7,9,11-tetraenyl]-5,6-dihydro-pyran-2-one