(2E,4S,6S,7S,8R,9E,11E,13E)-1-[(t-butyldimethylsilyl)oxy]-3,7,9,13-tetramethyl-8-methoxy-14-(2'-methyl-4'-oxazolyl)-6-(p-nitrobenzoate)-4-[(triisopropylsilyl)oxy]-2,9,11,13-tetradecatetraene

Base Information

• Chemical Name: (2E,4S,6S,7S,8R,9E,11E,13E)-1-[(t-butyldimethylsilyl)oxy]-3,7,9,13-tetramethyl-8-methoxy-14-(2'-methyl-4'-oxazolyl)-6-(p-nitrobenzoate)-4-[(triisopropylsilyl)oxy]-2,9,11,13-tetradecatetraene
• CAS No.: 237735-42-1
• Molecular Formula: C₄₅H₇₂N₂O₈Si₂
• Molecular Weight: 825.246
• Mol file: 237735-42-1.mol

Synonyms:(2E,4S,6S,7S,8R,9E,11E,13E)-1-[(t-butyldimethylsilyl)oxy]-3,7,9,13-tetramethyl-8-methoxy-14-(2'-methyl-4'-oxazolyl)-6-(p-nitrobenzoate)-4-[(triisopropylsilyl)oxy]-2,9,11,13-tetradecatetraene

Chemical Property of (2E,4S,6S,7S,8R,9E,11E,13E)-1-[(t-butyldimethylsilyl)oxy]-3,7,9,13-tetramethyl-8-methoxy-14-(2'-methyl-4'-oxazolyl)-6-(p-nitrobenzoate)-4-[(triisopropylsilyl)oxy]-2,9,11,13-tetradecatetraene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E,4S,6S,7S,8R,9E,11E,13E)-1-[(t-butyldimethylsilyl)oxy]-3,7,9,13-tetramethyl-8-methoxy-14-(2'-methyl-4'-oxazolyl)-6-(p-nitrobenzoate)-4-[(triisopropylsilyl)oxy]-2,9,11,13-tetradecatetraene

There total 25 articles about (2E,4S,6S,7S,8R,9E,11E,13E)-1-[(t-butyldimethylsilyl)oxy]-3,7,9,13-tetramethyl-8-methoxy-14-(2'-methyl-4'-oxazolyl)-6-(p-nitrobenzoate)-4-[(triisopropylsilyl)oxy]-2,9,11,13-tetradecatetraene 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: 77.0%

(2E,4S,6S,7S,8R,9E,11E,13E)-1-[(t-butyldimethylsilyl)oxy]-3,7,9,13-tetramethyl-14-(2'-methyl-4'-oxazolyl)-6-(p-nitrobenzoate)-4-[(triisopropylsilyl)oxy]-2,9,11,13-tetradecatetraen-8-ol (544429-53-0) + methyl iodide (74-88-4) → (2E,4S,6S,7S,8R,9E,11E,13E)-1-[(t-butyldimethylsilyl)oxy]-3,7,9,13-tetramethyl-8-methoxy-14-(2'-methyl-4'-oxazolyl)-6-(p-nitrobenzoate)-4-[(triisopropylsilyl)oxy]-2,9,11,13-tetradecatetraene (237735-42-1)

Guidance literature:

With silver(l) oxide; ultrasonication;

DOI:10.1016/S0040-4039(99)00731-5

Reference yield:

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) → (2E,4S,6S,7S,8R,9E,11E,13E)-1-[(t-butyldimethylsilyl)oxy]-3,7,9,13-tetramethyl-8-methoxy-14-(2'-methyl-4'-oxazolyl)-6-(p-nitrobenzoate)-4-[(triisopropylsilyl)oxy]-2,9,11,13-tetradecatetraene (237735-42-1)

Guidance literature:

Multi-step reaction with 10 steps

1: 99 percent / 2,6-lutidine

2: 89 percent / DIBAL

3: 1) Et₃N, 2) imidazol, 3) DIBAL

4: 90 percent / Dess-Martin reagent

5: 100 percent

6: 96 percent / Dess-Martin reagent

7: 85 percent / Ba(OH)2*H₂O

8: 86 percent / H₂SiF₆ / propan-2-ol / -40 °C

9: 83 percent / SmI₂

10: 77 percent / Ag₂O / ultrasonication

With 1H-imidazole; 2,6-dimethylpyridine; barium dihydroxide; fluorosilicic acid; samarium diiodide; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; silver(l) oxide; In isopropyl alcohol;

DOI:10.1016/S0040-4039(99)00731-5

Reference yield:

tert-butyldimethylsiloxyacetaldehyde (102191-92-4) → (2E,4S,6S,7S,8R,9E,11E,13E)-1-[(t-butyldimethylsilyl)oxy]-3,7,9,13-tetramethyl-8-methoxy-14-(2'-methyl-4'-oxazolyl)-6-(p-nitrobenzoate)-4-[(triisopropylsilyl)oxy]-2,9,11,13-tetradecatetraene (237735-42-1)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 84 percent / benzene / 48 h / 0 - 20 °C

2.1: diisopropylamine; n-BuLi / tetrahydrofuran / 1 h / -78 °C

2.2: 78 percent / tetrahydrofuran / 0.08 h

3.1: (-)-diisopropyl tartrate; Ti(O-iPr)4; tert-butylhydroperoxide / molecular sieves 3 Angstroem / CH₂Cl₂ / 20 h / -20 °C

3.2: 40 percent / FeSO₄; citric acid / H₂O; CH₂Cl₂

4.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0.08 h / 0 °C

5.1: 89 percent / DIBAL-H / CH₂Cl₂; toluene / 0.25 h / -95 °C

6.1: triethylamine; dicyclohexylboron triflate / CH₂Cl₂; hexane / 2 h / -78 °C

6.2: CH₂Cl₂; hexane / 3 h / -78 - 0 °C

6.3: 81 percent / NaOAc; water; H₂O₂ / CH₂Cl₂; hexane; methanol / 12 h

7.1: 86 percent / imidazole / CH₂Cl₂ / 0.08 h / 0 °C

8.1: 100 percent / DIBAL-H / CH₂Cl₂; toluene / 0.08 h / 0 °C

9.1: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h / 20 °C

10.1: t-BuLi / tetrahydrofuran; pentane / 0.75 h / -78 °C

10.2: 100 percent / tetrahydrofuran; pentane / 0.17 h

11.1: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 0 °C

12.1: Ba(OH)2 / tetrahydrofuran / 0.5 h / 20 °C

12.2: 85 percent / tetrahydrofuran; H₂O / 48 h

13.1: 86 percent / H₂SiF₆ / propan-2-ol; H₂O / 0.02 h / -40 °C

14.1: 83 percent / SmI₂ / tetrahydrofuran / 3.5 h / -10 °C

15.1: 77 percent / Ag₂O; molecular sieves 3 Angstroem / benzene / 12 h / sonication

With 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; barium dihydroxide; n-butyllithium; fluorosilicic acid; samarium diiodide; (-)-diisopropyl tartrate; 3 A molecular sieve; tert.-butyl lithium; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; diisopropylamine; silver(l) oxide; dicyclohexyl(((trifluoromethyl)sulfonyl)oxy)borane; 3 A molecular sieve; In tetrahydrofuran; hexane; dichloromethane; water; isopropyl alcohol; toluene; pentane; benzene; 1.1: Wittig olefination;

DOI:10.1021/jo034011x

upstream raw materials:

(2E,4S,6S,7S,8R,9E,11E,13E)-1-[(t-butyldimethylsilyl)oxy]-3,7,9,13-tetramethyl-14-(2'-methyl-4'-oxazolyl)-6-(p-nitrobenzoate)-4-[(triisopropylsilyl)oxy]-2,9,11,13-tetradecatetraen-8-ol

methyl iodide

tert-butyldimethylsiloxyacetaldehyde

(Z)-1,4-bis(tert-butyldimethylsilanyloxy)but-2-ene

Downstream raw materials:

(2E,4S,6S,7S,8R,9E,11E,13E)-3,7,9,13-tetramethyl-8-methoxy-14-(2'-methyl-4'-oxazolyl)-6-(p-nitrobenzoate)-4-[(triisopropylsilyl)oxy]-2,9,11,13-tetradecatetraen-1-al

4-nitro-benzoic acid 1-{7-[6-(tert-butyl-dimethyl-silanyloxy)-4-(2-triethylsilanyloxy-ethyl)-tetrahydro-pyran-2-yl]-3-methyl-2-triisopropylsilanyloxy-octa-3,5-dienyl}-3-methoxy-2,4,8-trimethyl-9-(2-methyl-oxazol-4-yl)-nona-4,6,8-trienyl ester

4-nitro-benzoic acid 1-{7-[4-(3-ethoxycarbonyl-allyl)-6-methoxy-tetrahydro-pyran-2-yl]-3-methyl-2-triisopropylsilanyloxy-octa-3,5-dienyl}-3-methoxy-2,4,8-trimethyl-9-(2-methyl-oxazol-4-yl)-nona-4,6,8-trienyl ester

(2E,4S,6S,7S,8R,9E,11E,13E)-3,7,9,13-tetramethyl-8-methoxy-14-(2'-methyl-4'-oxazolyl)-6-(p-nitrobenzoate)-4-[(triisopropylsilyl)oxy]-2,9,11,13-tetradecatetraen-1-ol

Refernces

• 1、 Lafontaine, Jennifer A.,Provencal, David P.,Gardelli, Cristina,Leahy, James W.. "The enantioselective total synthesis of the antitumor macrolide natural product rhizoxin D". . p. 4145 - 4148. Retrieved 2007/10/03.