ChemicalBook CAS DataBase List N-[6-[[5-[(3aS,4S,6aR)-Hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-4-yl]-1 -oxopentyl]amino]hexyl]-carbamic Acid 1,1-Dimethylethyl Ester

N-[6-[[5-[(3aS,4S,6aR)-Hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-4-yl]-1 -oxopentyl]amino]hexyl]-carbamic Acid 1,1-Dimethylethyl Ester synthesis

6synthesis methods

Product Name:N-[6-[[5-[(3aS,4S,6aR)-Hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-4-yl]-1 -oxopentyl]amino]hexyl]-carbamic Acid 1,1-Dimethylethyl Ester
CAS Number:153162-70-0
Molecular formula:C21H38N4O4S
Molecular Weight:442.62

51857-17-1 Synthesis

51857-17-1
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35013-72-0 Synthesis

35013-72-0
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N-[6-[[5-[(3aS,4S,6aR)-Hexahydro-2-oxo-1H-thieno[3,4-d]imidazol-4-yl]-1 -oxopentyl]amino]hexyl]-carbamic Acid 1,1-Dimethylethyl Ester

153162-70-0
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Yield:153162-70-0 90%

Reaction Conditions:

with triethylamine in N,N-dimethyl-formamide at 20;

Steps:

2.2.2. Synthesis of tert-butyl(6-(5-((3aS,4S,6aR)-2-oxohexahydro-1H- thieno[3,4-d]imidazol-4-yl)pentanamido)hexyl)carbamate (N-Boc-HDA- biotin)

N-Boc-HDA-biotin was synthesized as described in previous publications [53,54]. Briefly, NHS-biotin (3.00 g, 8.8 mmol) and N-Boc-1,6- hexanediamine (1.90 g, 8.8 mmol) were dissolved in anhydrous DMF (150 mL) and then TEA (1.22 mL, 12.0 mmol) was added. The reaction mixture was stirred at room temperature overnight. The product was isolated by precipitation in cold diethyl ether, dried under vacuum to yield N-Boc-HDA-biotin (3.50 g, 90%). 1H NMR (600 MHz, DMSO-d6) δ (ppm): 7.72 (t, 1H, J = 5.6 Hz, NH), 6.75 (t, 1H, J = 5.8 Hz, NH), 6.41 (s, 1H, NH-biotin), 6.35 (s, 1H, NH-biotin), 4.30 (ddt, 1H, J = 7.6, 5.2, 1.1 Hz, CHNH), 4.12 (ddd, 1H, J = 7.7, 4.4, 1.9 Hz, CHNH), 3.09 (ddd, 1H, J = 8.7, 6.2, 4.4 Hz, SCHCH2), 3.00 (q, 2H, NCH2), 2.85-2.90 (m, 2H, NCH2), 2.82 (dd, 1H, J = 12.4, 5.1 Hz, SCHH), 2.57 (d, 1H, J = 12.4 Hz, SCHH), 2.04 (t, 2H, J = 7.4 Hz, CH2C(=O)), 1.38-1.61 (m, 23H, 7CH2, C(CH3)3). ESI-MS m/z 443.2 (M + H)+, 465.2 (M + Na)+, calculated for C21H38N4O4S 442.6.

References:

Wang, Yan;van Steenbergen, Mies J.;Beztsinna, Nataliia;Shi, Yang;Lammers, Twan;van Nostrum, Cornelus F.;Hennink, Wim E. [Journal of Controlled Release,2020,vol. 328,p. 970 - 984]

51857-17-1 Synthesis

51857-17-1
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58-85-5 Synthesis