478920-22-8

Basic information

• Product Name: 7-methyl 1-[2-(trimethylsilyl)ethyl] (2S,6R)-N^α-(N-benzyloxycarbonyl-D-isoglutamyl α-methyl ester)-N^ε-(tert-butyloxycarbonyl)-2,6-diaminopimelate
• CAS NO: 478920-22-8
• Molecular Weight: 681.856
• Mol File: 478920-22-8.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 7-methyl 1-[2-(trimethylsilyl)ethyl] (2S,6R)-N^α-(N-benzyloxycarbonyl-D-isoglutamyl α-methyl ester)-N^ε-(tert-butyloxycarbonyl)-2,6-diaminopimelate(CAS DataBase Reference)
• NIST Chemistry Reference: 7-methyl 1-[2-(trimethylsilyl)ethyl] (2S,6R)-N^α-(N-benzyloxycarbonyl-D-isoglutamyl α-methyl ester)-N^ε-(tert-butyloxycarbonyl)-2,6-diaminopimelate(478920-22-8)
• EPA Substance Registry System: 7-methyl 1-[2-(trimethylsilyl)ethyl] (2S,6R)-N^α-(N-benzyloxycarbonyl-D-isoglutamyl α-methyl ester)-N^ε-(tert-butyloxycarbonyl)-2,6-diaminopimelate(478920-22-8)

Safety Data

• Hazardous Substances Data: 478920-22-8(Hazardous Substances Data)

Upstream product

• 478920-11-5 1-methyl 7-[2-(trimethylsilyl)] (Z,S)-6-[(benzyloxycarbonyl)-amino]-2-[(tert-butyloxycarbonyl)amino]-2-heptenedioate 
• 160806-00-8 7-methyl 1-[2-(trimethylsilyl)ethyl] (2S,6R)-N^α-benzyloxycarbonyl-N^ε-(tert-butyloxycarbonyl)-2,6-diaminopimelate 
• 160579-23-7 methyl (Z,S)-5-(3-benzyloxycarbonyl-5-oxo-1,3-oxazolidin-4-yl)-2-[(tert-butyloxycarbonyl)amino]-2-pentenoate 
• 115141-89-4 (4S)-3-(benzyloxycarbonyl)-4-(3-hydroxypropyl)-1,3-oxazolidin-5-one 
• 58456-26-1 (S)-4-<2'-(Chloroformyl)ethyl>-5-oxooxazolidin-3-carbonsaeure-benzylester 
• 89969-26-6 (S)-3-(3-benzyloxycarbonyl-5-oxo-1,3-oxazolidin-4-yl)propionaldehyde 
• 2916-68-9 2-(Trimethylsilyl)ethanol 
• 26566-11-0 N-(benzyloxycarbonyl)-D-glutamic acid 1-methyl ester 

Downstream Products

• 478920-33-1 1,6-anhydro-2-azido-4-O-benzyl-2-deoxy-3-O-{(2R)-propionyl-[L-alanyl-(D-isoglutamyl α-methyl ester)-(7-methyl)-1-(2-trimethylsilylethyl) (2S,6R)-N^ε-(tert-butyloxycarbonyl)-2,6-diaminopimelate]-2-yl}-β-D-glucopyranose 
• 478920-24-0 (2S,6R)-2-[(R)-4-((S)-2-Benzyloxycarbonylamino-propionylamino)-4-methoxycarbonyl-butyrylamino]-6-tert-butoxycarbonylamino-heptanedioic acid 7-methyl ester 1-(2-trimethylsilanyl-ethyl) ester 

Relevant articles and documents

Synthesis of muramyl peptides containing meso-diaminopimelic acid

Chain-extension of L-glutamate aldehyde 3 by means of the Wittig-Horner reaction furnished the desired C7 dicarboxylic acid derivative, which in turn, after C-C double bond hydrogenation and protecting group manipulation, afforded the 2,6-diaminopimelic acid derivatives (S,R)-9 and (S,S)-9, both with the desired orthogonal protecting group pattern. Synthesis of the muramic acid derivative 15 and attachment of an L-alanine residue furnished muramyl-L-alanine 18. The corresponding 1,6-anhydromuramic acid derivative 26 was obtained similarly. Treatment of these compounds with peptides 28-30 and with the 2,6-diaminopimelic acid containing di- and tripeptides 32a, 32b, and 35 gave the protected muramyl peptides 17, 37, 40, 42, 44, 46, and 49a and 49b, which, after deprotection, afforded the desired target molecules muramyl-L-alanine (38), muramyl-L-alanyl-D-glutamic acid (39), muramyl-L-alanyl-D-glutaminide (41), muramyl-L-alanyl-D- isoglutaminyl-L-lysine (43), muramyl-L-alanyl-D-isoglutaminyl-(2S,6R)-2,6-diaminopimelic acid (45), muramyl-L-alanyl- L-isoglutaminyl-(2S,6R)-2,6-diaminopimelic-D-alanme (47), 1,6-anhydromuramyl-L-alanyl-D-isoglutaminyl-(2S,6R)-2,6-diaminopimelic acid (50a), and 1,6-anhydromuramyl-L-alanyl-D- isoglutaminyl-(2S,6S)-2,6-diaminiopimelic acid (50b). ( Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002).