112302-93-9

Upstream product

• 66111-51-1 Tert-butoxycarbonyl-L-2-aminobutanoyl-D-isoglutamine benzyl ester 
• 112302-94-0 N-(tert-butoxycarbonyl)-L-α-aminobutanoyl-D-isoglutamine 
• 76-05-1 trifluoroacetic acid 

Downstream Products

• 210631-18-8 (R)-4-{(S)-2-[2-((4aR,6S,7R,8R,8aS)-7-Acetylamino-6-benzyloxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy)-acetylamino]-butyrylamino}-4-carbamoyl-butyric acid benzyl ester 
• 112302-97-3 N-<2-O--glycoloyl>-L-α-aminobutanoyl-D-isoglutamine benzyl ester 
• 141989-33-5 N-<2-O--glucoloyl>-L-α-aminobutanoyl-D-isoglutamine benzyl ester 

Relevant academic research and scientific papers

Synthesis of normuramic acid Carba analog and its glycopeptide derivative resistant to β-elimination splitting of the side chain

Carba analogs of normuramic acid, i.e., 3-(benzyl 2-acetamido-2,3-dideoxy-4,6-O-iso-propylidene-α-D-glucopyranosid-3-yl) propanoic acid derivatives (nitrile or esters) 3a-3c were prepared by addition of radicals generated from benzyl 2-acetamido-2-deoxy-4,6-O-iso-propylidene-3-O-[(methylsulfanyl)thiocarbonyl]- (2a) or -3-O-(phenoxythiocarbonyl)-α-D-glucopyranoside (2b) with Bu3SnH to acrylonitrile or acryl esters. Alkaline hydrolysis of ethyl ester 3c afforded 3-(benzyl 2-acetamido-2,3-dideoxy-4,6-O-isopropylidene-α-D-glucopyranosid-3-yl) propanoic acid (5). Coupling of acid 5 with L-2-aminobutanoyl-D-isoglutamine benzyl ester trifluoroacetate and subsequent deprotection of the intermediate 6 furnished N-[3-(2-acetamido-2,3-dideoxy-α-D-glucopyranosid-3-yl)propanoyl]-L-2- amino-butanoyl-D-isoglutamine (7).

Synthesis and immunomodulating activity of lipophilic analogs of N-acetylnormuramoyl-L-2-aminobutanoyl-D-isoglutamine

N-Acetylnormuramoyl-L-2-aminobutanoyl-D-isoglutamine (7) and its lipophilic 6-O-octadecanoyl (8) and 6-O-(2-tetradecylhexadecanoyl) (9) derivatives were prepared and their immunoadjuvant activity and pyrogenicity were tested. Compounds 8 and 9 are less pyrogenic than muramoyl-dipeptide (MDP) and norMDP analog 7. Both lipophilic derivatives 8 and 9 are better adjuvants than MDP in cell mediated immunity.

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.

SYNTHESIS OF O-(2-DEOXY-2-STEAROYLAMINO-β-D-GLUCOPYRANOSYL)-(14)-N-ACETYLNORMURAMOYL-L-α-AMINOBUTANOYL-D-ISOGLUTAMINE, A LIPOPHILIC DISACCHARIDE ANALOGUE OF MDP

Partial N-deacetylation of compound II with barium hydroxide afforded benzyl 2-acetamido-3-O-allyl-4-O-(2-amino-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranosyl)-6-O-benzyl-2-deoxy-α-D-glucopyranoside (III) in high yield.Compound III was N-acylated with st

THE SYNTHESIS OF O-(2-ACETAMIDO-2-DEOXY-β-D-GLUCOPYRANOSYL)-(1->4)-N-ACETYLNORMURAMOYL-L-α-AMINOBUTANOYL-D-ISOGLUTAMINE

Benzyl 2-acetamido-3-O-allyl-6-O-benzyl-2-deoxy-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-α-D-glucopyranoside (4) was obtained in high yield on using the silver triflate method in the absence of base.Compound 4 was converted in six