ChemicalBook CAS DataBase List Biotin-PEG4-N3

Biotin-PEG4-N3 synthesis

8synthesis methods

Product Name:Biotin-PEG4-N3
CAS Number:875770-34-6
Molecular formula:C18H32N6O5S
Molecular Weight:444.55

35013-72-0 Synthesis

35013-72-0
360 suppliers
$12.00/100mg

134179-38-7
208 suppliers
$39.20/100MG

875770-34-6
125 suppliers
$28.00/5mg

Yield:875770-34-6 100%

Reaction Conditions:

in N,N-dimethyl-formamide at 20;

Steps:

2.5 Preparation of N-(2-(2-(2-(2-azidoethoxy) ethoxy) ethoxy) ethyl)-5-(2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl) pentanamide (Biotin-N₃, (6))

Biotin-OSuc (14) (187 mg, 0.55 mmol) was completely dissolved in DMF (5 mL) with gentle warming.
After slowly cooling the solution to room temperature without recurring precipitation, the 11-azido-3,6,9-trioxaundecan-1-amine (
Borcard et al., 2011
) (109 mg, 0.50 mmol) was added.
The reaction proceeded at room temperature overnight with stirring and the reaction products were concentrated under vacuum.
The remaining solid was triturated in CH₂Cl₂/Et₂O (30/70) solution and the white solid was filtered to obtain N-(2-(2-(2-(2-azidoethoxy) ethoxy) ethoxy) ethyl)-5-(2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl) pentanamide (6) (219 mg; quant.); ¹H NMR (300 MHz, DMSO-d₆): δ 6.43-6.38 (s, 1H, NH), 6.37-6.34 (s, 1H, NH), 4.33-4.25 (m, 1H), 4.12-4.09 (m, 1H), 3.62-3.34 (m, 12H), 3.12-3.08 (m, 1H), 2.89-2.78 (m, 4H), 1.55-1.19 (m, 6H); ¹³C NMR (100 MHz, CDCl₃): δ 25.6, 28.0, 28.1, 35.9, 39.2, 40.5, 50.7, 55.5, 60.3, 61.8, 70.0, 70.1, 70.4, 70.5, 70.6, 163.9, 173.5; LRMS (ESI) m/z calcd for C₁₈H₃₂N₆O₅SH⁺ 445.2; found 445.2.

References:

Salomé, Christophe;Spanedda, Maria Vittoria;Hilbold, Benoit;Berner, Etienne;Heurtault, Béatrice;Fournel, Sylvie;Frisch, Benoit;Bourel-Bonnet, Line [Chemistry and Physics of Lipids,2015,vol. 188,art. no. 4354,p. 27 - 36]

134179-38-7
208 suppliers
$39.20/100MG

58-85-5 Synthesis