132388-69-3

Basic information

• Product Name: N-Boc-N'-trityl-L-glutamine
• 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
• CAS NO: 132388-69-3
• Molecular Formula: C₂₉H₃₂N₂O₅
• Molecular Weight: 488.57
• Product Categories: Amino Acid Derivatives;Glutamine [Gln, Q];Boc-Amino Acids and Derivative;Boc-Amino acid series
• Mol File: 132388-69-3.mol

Chemical Properties

• Boiling Point: 728.9 °C at 760 mmHg
• Flash Point: 394.6 °C
• Appearance: /
• Density: 1.188 g/cm³
• Vapor Pressure: 2.2E-20mmHg at 25°C
• Refractive Index: 1.587
• Storage Temp.: Store at RT.
• BRN: 4340082
• CAS DataBase Reference: N-Boc-N'-trityl-L-glutamine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Boc-N'-trityl-L-glutamine(132388-69-3)
• EPA Substance Registry System: N-Boc-N'-trityl-L-glutamine(132388-69-3)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 132388-69-3(Hazardous Substances Data)

Usage

Chemical Properties

White powder

InChI:InChI=1/C29H32N2O5/c1-28(2,3)36-27(35)22-16-10-11-17-23(22)29(20-12-6-4-7-13-20,21-14-8-5-9-15-21)31-24(26(33)34)18-19-25(30)32/h4-17,24,31H,18-19H2,1-3H3,(H2,30,32)(H,33,34)/t24-/m1/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 102747-84-2 5-trityl-L-glutamine 
• 76-84-6 triphenylmethyl alcohol 
• 56-85-9 L-glutamine 
• 2650-64-8 Cbz-L-Gln 
• 132388-60-4 (S)-2-(((benzyloxy)carbonyl)amino)-5-oxo-5-(tritylamino)pentanoic acid 

Downstream Products

• 210428-12-9 2-tert-butoxycarbonylamino-4-(tritylcarbamoyl)butyric acid methyl ester 
• 199005-56-6 [(S)-1-(Methoxy-methyl-carbamoyl)-3-(trityl-carbamoyl)-propyl]-carbamic acid tert-butyl ester 
• 199005-58-8 (S,E)-ethyl 4-(tert-butoxycarbonylamino)-7-oxo-7-(tritylamino)-hept-2-enoate 
• 199005-57-7 Boc-Gln(Trt)-H 
• 817208-62-1 [3-tert-butoxycarbonylamino-2-oxo-5-(tritylcarbamoyl)pentyl]phosphonic acid dimethyl ester 
• 817208-65-4 5-tert-butoxycarbonylamino-2-[3-(tert-butyldimethylsilanyloxy)propyl]-4-oxo-7-(tritylcarbamoyl)hept-2-enoic acid methyl ester 
• 222409-74-7 methyl (3S)-3-(Boc-amino)-6-oxo-(tritylamino)hexanoate 
• 222409-82-7 methyl (2S,3S)-3-(Boc-amino)-2-<(4-methoxybenzyl)sulfanyl>-6-oxo(tritylamino)hexanoate 
• 222409-89-4 (2SR,3S)-3-(Boc-amino)-2-<(4-methoxybenzyl)sulfanyl>-6-oxo(tritylamino)hexanoic acid 

Relevant articles and documents

Protected amino acids and process for the preparation thereof

Compounds of the formula I, STR1 in which 'R1 is an amino protective group, and n stands for 1 or 2, R1 denotes hydrogen or an amino protective group, R2 denotes hydrogen or a carboxyl protective group and R3 denotes triphenylmethyl, 4-monomethoxy-trityl or 4,4'-dimethoxy-trityl, and reactive carboxylic acid derivatives of such compounds of the formula I in which R2 stands for hydrogen, are described. These compounds can be used as starting materials for the preparation of peptides. They are more suitable for this than are analogous compounds of the formula I in which R3 denotes hydrogen or one of the carbamoyl protective groups hitherto customary.

Protection of carboxamide functions by the trityl residue. Application to peptide synthesis

Carboxamide functions may be tritylated by an acid-catalyzed reaction with triphenylmethanol and acetic anhydride in glacial acetic acid. The ω-trityl group of asparagine and glutamine is cleavable by TFA, but stable to strong mineral acids in aqueous solution, as well as to nucleophiles and bases. In peptide syntheses, it is ideally suited for combination with side-chain protections of the t.butyl-type.