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| | Boc-tota Basic information |
| Product Name: | Boc-tota | | Synonyms: | 1-(T-BUTYLOXYCARBONYL-AMINO)-4,7,10-TRIOXA-13-TRIDECANAMINE;1-(TERT-BUTYLOXYCARBONYL-AMINO)-4,7,10-TRIOXA-13-TRIDECANAMINE;3-[2-(2-(3-(BOC-AMINO)PROPYLOXY)ETHOXY)ETHOXY]PROPYLAMINE;BOC-1-AMINO-4,7,10-TRIOXA-13-TRIDECANAMINE;N-Boc-4,7,10-trioxa-1,13-tridecanediamine >=95.0% (NT);tert-butyl N-[3-[2-[2-(3-aminopropoxy)ethoxy]ethoxy]propyl]carbamate;tert-Butyl (3-(2-(2-(3-aminopropoxy)ethoxy) 194920-62-2;CAS_194920-62-2 | | CAS: | 194920-62-2 | | MF: | C15H32N2O5 | | MW: | 320.42 | | EINECS: | | | Product Categories: | peg | | Mol File: | 194920-62-2.mol |  |
| | Boc-tota Chemical Properties |
| 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) | | pka | 12.66±0.46(Predicted) | | form | Oil | | color | Colourless | | InChI | 1S/C15H32N2O5/c1-15(2,3)22-14(18)17-7-5-9-20-11-13-21-12-10-19-8-4-6-16/h4-13,16H2,1-3H3,(H,17,18) | | InChIKey | WHHYAYNALHPDGJ-UHFFFAOYSA-N | | SMILES | NCCCOCCOCCOCCCNC(OC(C)(C)C)=O |
| WGK Germany | 3 | | F | 10-34 | | HS Code | 2924190090 | | Storage Class | 10 - Combustible liquids |
| | Boc-tota Usage And Synthesis |
| 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 |
| | Boc-tota Preparation Products And Raw materials |
| Raw materials | 4,7,10-Trioxa-1,13-tridecanediamine-->Di-tert-butyl dicarbonate | | Preparation Products | [3aS-(3aalpha,4beta,6aalpha)]-N-[3-[2-[2-(3-Aminopropoxy)ethoxy]ethoxy]propyl]hexahydro-2-oxo-1H-thieno[3,4-d]imidazole-4-pentanamide mono(trifluoroacetate)-->Boc-TOTA-N3-->6,9,12-Trioxa-2,16-diazaoctadecanoic acid, 18-chloro-17-oxo-, 1,1-dimethylethyl ester |
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