N-Boc-N'-trityl-L-glutamine
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N-Boc-N'-trityl-L-glutamine
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CAS No:
132388-69-3
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Formula:
C29H32N2O5
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Chemical Name:
N-Boc-N'-trityl-L-glutamine
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Synonyms:
N-ALPHA-BOC-N-DELTA-TRITYL-L-GLUTAMINE;N-ALPHA-T-BOC-GAMMA-TRITYL-L-GLUTAMINE;N-ALPHA-T-BUTOXYCARBONYL-N-GAMMA-TRITYL-L-GLUTAMINE;BOC-GLN(TRT)-OH;BOC-L-GLUTAMINE(TRITYL);BOC-N-DELTA-TRITYL-L-GLUTAMINE;BOC-L-TRITYL GLUTAMINE;Nα-Boc-Nδ-trityl-L-glutamine
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CAS No:
N-Boc-N'-trityl-L-glutamine Use and Manufacturing
Compound S5 (100 mg, 0.2 mmol) was dissolved in 2 mL dry DMF at 0C, and Boc-Gln (Trt)-OH (80 mg, 0.2 mmol), HOBt (63 mg, 0.4 mmol) HOBt and EDC (80 mg, 0.4 mmol) were added. DIPEA (70 muL, 0.4 mmol) was added and thepH of the solution controlled by further small additions of DIPEA. The reaction mixture was allowed to warm to rt andwas stirred overnight. dH2O (10 mL) was added and the suspension extracted with EtOAc (3 x 25 mL). The combinedorganic layers were washed with dH2O (100 mL) and brine (100 mL), dried with Na2SO4, and evaporated. The crudematerial was purified by flash chromatography using CH2Cl2/MeOH (90 %).General procedure: Into a 10 ml round-bottomed flask was added sequentially compound 7 (0.07 mmol), Protected amino acid R1COOH(0.57 mmol), and 4 ml of ACN was added. After stirring the mixture at 0 C for about 2 min, EDC (0.57 mmol) was addedfollowed by DMAP (0.07 mmol). The mixture was stirred at room temperature for 6h, leading to the consumption of the starting material as indicated by TLC. ACNwas removed in vacuo and about 50 ml DCM was added to desolve the residue. TheDCM solution was washed sequentially with water (100 ml x 2), dilute HCl (1 %, 100 ml x 2), saturated NaHCO3 (100 ml x 1), and saturated sodiumchloride (100 ml x 1), and dried over anhydrous sodium sulphate. The solvent(DCM) was then removed in vacuo and the crude product was purified bysilica-gel column chromatography (DCM/MeOH: 150/1, 150/2) to obtain a yellowsolid.
Computed Properties
Molecular Weight:488.6
XLogP3:4.8
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:11
Exact Mass:488.23112213
Monoisotopic Mass:488.23112213
Topological Polar Surface Area:105
Heavy Atom Count:36
Complexity:683
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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