# Approaches to the Functionalization of Organosilicon Dendrones Based on Limonene
## 2 Experimental
### Material and Methods
The filtrate was evaporated to remove the solvents, and the residue was dissolved in hexane and passed through silica. Solvent was removed by evaporation under reduced pressure. \(\phi\) = 78%. For C\({}_{35}\)H\({}_{74}\)Si\({}_{3}\): C 72.51%; H 12.78%; Si 14.50%: C 72.52%; H 12.64%; Si 14.30%. _3-Chloropropyldimethylsilane_  
This compound was synthesized according to the method published in [45]. Yield of the product was 72%. \({}^{1}\)H NMR (300 MHz, Chloroform-d) \(\delta\): 3.87 (m, 1H, Si\(\underline{\text{H}}\)), 3.52 (t, J = 6.9 Hz, 2H, CH\(\underline{\text{H}}\)), 1.89-1.73 (m, 2H, CH\(\underline{\text{H}}\)), 0.77-0.63 (m, 2H, CH\(\underline{\text{H}}\)), 0.09 (d, J = 3.5 Hz, 6H, SiCH\(\underline{\text{H}}\)). _Bis(3-chloropropyldimethylsilylpropyl)methylsilyllimonene (Lim-G0(PrCl)2)_  
To a stirred RM of 1.14 g (0.0084 mol) of 3-chloropropyldimethylsilane and 1.0 g (0.0038 mol) of _Lim-G\({}_{0}\)All\({}_{2}\)_, purged with argon, 11 mL dry toluene and 11 \(\mu\)L of Pt\({}_{2}\)(DVDS)\({}_{3}\) were added. RM was stirred at 60 \({}^{\circ}\)C for 10 h. After reaction completed, substance was evaporated to remove the solvents, and the residue was evacuated (0.5 mbar) at 70 \({}^{\circ}\)C. \(\phi\) = 99%. _Tris(3-chloropropyldimethylsilylpropyl)silyllimonene (Lim-G1(PrCl)3)_  
This compound was obtained similarly to _Lim-G\({}_{1,5}\)Cl\({}_{2}\)_ from 1.0 g (0.0035 mol) _Lim-G\({}_{0}\)All\({}_{3}\)_, 1.56 g (0.0114 mol) _3-chloropropyldimethylsilane_, 13 \(\mu\)L of Pt\({}_{2}\)(DVDS)\({}_{3}\), and 13 mL anhydrous toluene. \(\phi\) = 99%. _Dendrimer of the 2.5 generation (Lim-G2(PrCl)4)_  
This compound was obtained similarly to _Lim-G\({}_{1,5}\)Cl\({}_{2}\)_ from 1.0 g (0.0019 mol) _Lim-G\({}_{1}\)All\({}_{4}\)_, 1.17 g (0.0085 mol) _3-chloropropyldimethylsilane_, 12 \(\mu\)L of Pt\({}_{2}\)(DVDS)\({}_{3}\), and 12 mL anhydrous toluene. Yield of the product was 99%. _Bis(3-azidopropyldimethylsilylpropyl)methylsilyllimonene (Lim-G0(PrN3)2)_  
To a stirred RM of 1.5 g (0.0028 mol) of _Lim-G\({}_{1.5}\)Cl\({}_{2}\)_ and 0.44 g (0.0067 mol) of sodium azide, 7.5 mL dry DMF was added. RM was stirred at 70 \({}^{\circ}\)C for 6 h. After reaction finished, the product was extracted with toluene and washed with distilled water three times. Organic layer was dried over Na\({}_{2}\)SO\({}_{4}\). Solvent was removed by evaporation under reduced pressure. \(\phi\) = 92%. _Tris(3-azidopropyldimethylsilylpropyl)silyllimonene (Lim-G1(PrN3)3)_  
This compound was obtained similarly to _Lim-G\({}_{1.5}\)(N\({}_{3}\))\({}_{2}\)_ from 1.5 g (0.0021 mol) _Lim-G\({}_{1.5}\)Cl\({}_{3}\)_, 0.50 g (0.0077 mol) sodium azide, and 7.5 mL anhydrous DMF. \(\phi\) = 89%. _CD of the 2.5 generation (Lim-G\({}_{2}\)(PrN\({}_{3}\))\({}^{4}\))_  
This compound was obtained similarly to _Lim-G\({}_{1.5}\)(N\({}_{3}\))\({}_{2}\)_ from 1.5 g (0.0014 mol) _Lim-G\({}_{2.5}\)Cl\({}_{4}\)_, 0.44 g (0.0068 mol) sodium azide, and 7.5 mL anhydrous DMF. \(\phi\) = 90%. _1,1,1,3,5,5-Hepmat methyl-3-(2-(3+-epoxy-4-methylyl)propyl)trisiloxane (LimOx-G0.5 TMS2)_  
To a stirred, ice-cold solution of _Lim-G\({}_{0.5}\)TMS\({}_{2}\)_ (2.0 g, 0.0056 mol) in DCM (100 mL), NaHCO\({}_{3}\) (0.94 g, 0.0112 mol) and _m_-CPBA (1.44 g 0.0084 mol) were added sequentially. The mixture was stirred at 0 \({}^{\circ}\)C for 30 min. Then, the process was stopped by addition of 0.3 M aqueous solution of Na\({}_{2}\)S\({}_{2}\)O\({}_{3}\) (200 mL) and extracted with dichloromethane (3 \(\times\) 50 mL). The combined organic phases were washed sequentially with a saturated aqueous NaHCO\({}_{3}\) solution (3 \(\times\) 100 mL) and brine (100 mL), dried over Na\({}_{2}\)SO\({}_{4}\), and concentrated under reduced pressure. \(\phi\) = 82%. _Bis(heptamethylsilylpropyl)methylsilyl-1,2-epoxy-limonene (LimOx-G1.STMS4)_  
This compound was synthesized similarly to _Lim-G\({}_{0.5}\)TMS\({}_{2}\)_O from 2.0 g (0.0028 mol) _Lim-G\({}_{1.5}\)TMS\({}_{4}\)_, 0.73 g (0.0042 mol) m-CPBA, 0.47 g (0.0057 mol) NaHCO\({}_{3}\), and 85 mL DCM. \(\phi\) = 85%.