(6E,10E,12E)(2R,3S,4R,5R,9R)-9-(tert-butyldimethyl-silanyloxy)-1-(3,4-dimethoxy-benzyloxy)-13-iodo-5-methoxy-2,4,7-trimethyl-3-triethylsilanyloxy-trideca-6,10,12-triene

Base Information

• Chemical Name: (6E,10E,12E)(2R,3S,4R,5R,9R)-9-(tert-butyldimethyl-silanyloxy)-1-(3,4-dimethoxy-benzyloxy)-13-iodo-5-methoxy-2,4,7-trimethyl-3-triethylsilanyloxy-trideca-6,10,12-triene
• CAS No.: 627101-49-9
• Molecular Formula: C₃₈H₆₇IO₆Si₂
• Molecular Weight: 803.022
• Mol file: 627101-49-9.mol

Synonyms:(6E,10E,12E)(2R,3S,4R,5R,9R)-9-(tert-butyldimethyl-silanyloxy)-1-(3,4-dimethoxy-benzyloxy)-13-iodo-5-methoxy-2,4,7-trimethyl-3-triethylsilanyloxy-trideca-6,10,12-triene

Chemical Property of (6E,10E,12E)(2R,3S,4R,5R,9R)-9-(tert-butyldimethyl-silanyloxy)-1-(3,4-dimethoxy-benzyloxy)-13-iodo-5-methoxy-2,4,7-trimethyl-3-triethylsilanyloxy-trideca-6,10,12-triene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6E,10E,12E)(2R,3S,4R,5R,9R)-9-(tert-butyldimethyl-silanyloxy)-1-(3,4-dimethoxy-benzyloxy)-13-iodo-5-methoxy-2,4,7-trimethyl-3-triethylsilanyloxy-trideca-6,10,12-triene

There total 15 articles about (6E,10E,12E)(2R,3S,4R,5R,9R)-9-(tert-butyldimethyl-silanyloxy)-1-(3,4-dimethoxy-benzyloxy)-13-iodo-5-methoxy-2,4,7-trimethyl-3-triethylsilanyloxy-trideca-6,10,12-triene 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:

trimethoxonium tetrafluoroborate (420-37-1) + (6E,10E,12E)(2R,3S,4R,5R,9R)-9-(tert-butyldimethyl-silanyloxy)-1-(3,4-dimethoxy-benzyloxy)-13-iodo-2,4,7-trimethyl-3-triethylsilanyloxy-trideca-6,10,12-trien-5-ol (627101-60-4) → (6E,10E,12E)(2R,3S,4R,5R,9R)-9-(tert-butyldimethyl-silanyloxy)-1-(3,4-dimethoxy-benzyloxy)-13-iodo-5-methoxy-2,4,7-trimethyl-3-triethylsilanyloxy-trideca-6,10,12-triene (627101-49-9)

Guidance literature:

With Proton Sponge; In dichloromethane; at 0 ℃;

DOI:10.1021/ol0357853

Reference yield:

(E)-((1-methoxy-3-methylbuta-1,3-dien-1-yl)oxy)trimethylsilane (76927-59-8) → (6E,10E,12E)(2R,3S,4R,5R,9R)-9-(tert-butyldimethyl-silanyloxy)-1-(3,4-dimethoxy-benzyloxy)-13-iodo-5-methoxy-2,4,7-trimethyl-3-triethylsilanyloxy-trideca-6,10,12-triene (627101-49-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 52 percent / titanium tetraisopropoxide; (R)-BINOL; molecular sieves 4 Angstroem / tetrahydrofuran / 14 h / -20 °C

2.1: imidazole / CH₂Cl₂

3.1: DIBAL / CH₂Cl₂ / -78 °C

4.1: MnO₂ / CH₂Cl₂

5.1: c-Hex₂BCl; Et₃N / diethyl ether / -20 °C

5.2: diethyl ether / -78 - -30 °C

6.1: SmI₂ / tetrahydrofuran / -20 °C

7.1: lutidine / CH₂Cl₂ / -78 °C

8.1: DIBAL / CH₂Cl₂ / -78 °C

9.1: proton sponge / CH₂Cl₂ / 0 °C

With 1H-imidazole; titanium(IV) isopropylate; manganese(IV) oxide; samarium diiodide; Proton Sponge; 4 A molecular sieve; lutidine; dicyclohexylboron chloride; (R)-1,1'-Bi-2-naphthol; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; 1.1: Mukaiyama aldol reaction;

DOI:10.1021/ol0357853

Reference yield:

triethylsilyl trifluoromethyl sulfonate (79271-56-0) → (6E,10E,12E)(2R,3S,4R,5R,9R)-9-(tert-butyldimethyl-silanyloxy)-1-(3,4-dimethoxy-benzyloxy)-13-iodo-5-methoxy-2,4,7-trimethyl-3-triethylsilanyloxy-trideca-6,10,12-triene (627101-49-9)

Guidance literature:

Multi-step reaction with 3 steps

1: lutidine / CH₂Cl₂ / -78 °C

2: DIBAL / CH₂Cl₂ / -78 °C

3: proton sponge / CH₂Cl₂ / 0 °C

With Proton Sponge; lutidine; diisobutylaluminium hydride; In dichloromethane;

DOI:10.1021/ol0357853

upstream raw materials:

trimethoxonium tetrafluoroborate

(6E,10E,12E)(2R,3S,4R,5R,9R)-9-(tert-butyldimethyl-silanyloxy)-1-(3,4-dimethoxy-benzyloxy)-13-iodo-2,4,7-trimethyl-3-triethylsilanyloxy-trideca-6,10,12-trien-5-ol

(E)-((1-methoxy-3-methylbuta-1,3-dien-1-yl)oxy)trimethylsilane

triethylsilyl trifluoromethyl sulfonate

Refernces