BOC-TOTA

BOC-TOTA Property

Boiling point:

432.4±35.0 °C(Predicted)

Density 

1.035 g/mL at 20 °C

storage temp. 

2-8°C

solubility 

Chloroform, Ethyl Acetate (Slightly)

form 

Oil

pka

12.66±0.46(Predicted)

color 

Colourless

Safety

WGK Germany 

3

F 

10-34

HS Code 

2924190090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

BOC-TOTA Chemical Properties,Usage,Production

Description

Boc-TOTA is a linker containing an amino group with a Boc-protected amino group. The amino group is reactive with carboxylic acids, activated NHS esters, carbonyls (ketone, aldehyde) etc. The Boc group can be deprotected under mild acidic conditions to form the free amine.

Uses

tert-Butyl (3-(2-(2-(3-Aminopropoxy)ethoxy)ethoxy)propyl)carbamate is used as a reactant in the synthesis of gallium-labeled PET imaging agents for CXCR4 for potential cancer diagnosis.

Uses

Protected linker.

reaction suitability

reagent type: cross-linking reagent

Synthesis

GENERAL STEPS: A solution of di-tert-butyl dicarbonate (1.99 g, 9.12 mmol) in dichloromethane (55 mL + 5 mL of rinse solution) was slowly added dropwise through the addition funnel to a solution of 4,7,10-trioxo-1,13-tridecanediamine (20 mL, 91.2 mmol) in dichloromethane (100 mL) at 0°C. The reaction mixture was gradually warmed to room temperature and stirred for 3 hours. After the dropwise addition, the reaction mixture was gradually warmed up to room temperature and stirring was continued for 3 hours. Upon completion of the reaction, the reaction was quenched with deionized water (100 mL). The organic and aqueous phases were separated, and the organic phase was washed sequentially with deionized water (3×50 mL) and saturated saline (50 mL), dried with anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to afford N-BOC-4,7,10-trioxa-1,13-tridecanediamine (2.571 g, 88% yield) as a colorless liquid. Thin layer chromatography (TLC) analysis: Rf = 0.14 (Expanding agent: 10% methanol, 0.5% ammonia in dichloromethane solution).1H-NMR (CDCl3, 400 MHz) data: δ 5.10 (broad single peak, 1H), 3.51-3.64 (multiple peaks, 12H), 3.61 (single peak, 4H), 3.21 (multiple peaks, 2H), 2.79 (triple peak, J = 6.7 Hz, 1H), 1.77-1.68 (multiple peaks, 4H), 1.42 (single peak, 9H) ppm.

IC 50

PEGs

References

[1] Chemical Communications, 2010, vol. 46, # 39, p. 7403 - 7405
[2] Bioconjugate Chemistry, 2013, vol. 24, # 12, p. 2058 - 2066
[3] Journal of the American Chemical Society, 2000, vol. 122, # 11, p. 2663 - 2664
[4] Angewandte Chemie - International Edition, 2007, vol. 46, # 11, p. 1798 - 1802
[5] European Journal of Organic Chemistry, 2004, # 9, p. 1983 - 2001