14595-22-3

Usage

Chemical Properties

Wjite Solid

InChI:InChI=1/C24H27NO8/c1-15(26)25-20-22(29-14-19(27)28)21-18(13-31-23(33-21)17-10-6-3-7-11-17)32-24(20)30-12-16-8-4-2-5-9-16/h2-11,18,20-24H,12-14H2,1H3,(H,25,26)(H,27,28)/t18?,20-,21+,22+,23?,24-/m0/s1

Upstream product

• 13343-63-0 benzyl 4,6-O-benzylidene-2-acetylamino-2-deoxy-α-D-glucopyranoside 
• 79-11-8 chloroacetic acid 

Downstream Products

• 87694-57-3 1-α-O-benzyl-4,6-O-benzylidene-N-acetylnormuramyl-α-aminobutyryl-D-isoglutaminyl-N^ε-p-toluenesulfonyllysyl-N^ε-p-toluenesulfonyllysyl-N^ε-p-tolueunesulfonyllysine amide 
• 129398-56-7 1-α-O-benzyl-4,6-O-benzylidine-N-acetyl-norMur-Aib-D-Glu(OBzl)-NH2 
• 124453-31-2 1-α-O-benzyl-4,6-O-benzylidene-N-acetylnormuramyl-L-α-aminobutyryl-D-glutamine n-butyl ester 

Relevant academic research and scientific papers

Synthesis of O--(14)-N-acetylnormuramoyl-L-α-aminobutanoyl-D-isoglutamine, lipophilic disaccharide analogues of MDP

Silver triflate-promoted condensation of 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide (1) with benzyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(methoxycarbonyl)methyl-α-D-glucopyranoside (4) afforded the key compound, benzyl 2-acetamido-6-O-benzyl-2-deoxy-3-O-(methoxycarbonyl)methyl-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-α-D-glucopyranoside (5), which after deprotection was transformed into acid 10.Condensation of 10 with the benzyl ester of L-α-aminobutanoyl-D-isoglutamine and deisopropylidenation of the product 11 afforded the benzyl ester of N-glycoloyl>-L-α-aminobutanoyl-D-isoglutamine (12).Partial O-acylation of 12 and hydrogenolysis of protecting groups gave the 6-O-stearoyl- and 6-O-(2-tetradecylhexadecanoyl)-disaccharide-dipeptides 17 and 18, respectively.Pyrogenicity and adjuvant activity in cell-mediated immunity are reported.