benzyl N²-(N-acetyl-1-O-benzyl-4,6-O-benzylidene-α-D-muramoyl)-L-alanyl-D-isoglutaminate

Base Information

• Chemical Name: benzyl N²-(N-acetyl-1-O-benzyl-4,6-O-benzylidene-α-D-muramoyl)-L-alanyl-D-isoglutaminate
• CAS No.: 59573-84-1
• Molecular Formula: C₄₀H₄₈N₄O₁₁
• Molecular Weight: 760.841
• Mol file: 59573-84-1.mol

Synonyms:benzyl N²-(N-acetyl-1-O-benzyl-4,6-O-benzylidene-α-D-muramoyl)-L-alanyl-D-isoglutaminate

Chemical Property of benzyl N²-(N-acetyl-1-O-benzyl-4,6-O-benzylidene-α-D-muramoyl)-L-alanyl-D-isoglutaminate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl N²-(N-acetyl-1-O-benzyl-4,6-O-benzylidene-α-D-muramoyl)-L-alanyl-D-isoglutaminate

There total 13 articles about benzyl N²-(N-acetyl-1-O-benzyl-4,6-O-benzylidene-α-D-muramoyl)-L-alanyl-D-isoglutaminate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

tert-butoxycarbonyl-L-alanyl-D-isoglutamine benzyl ester (18814-49-8) → benzyl N2-(N-acetyl-1-O-benzyl-4,6-O-benzylidene-α-D-muramoyl)-L-alanyl-D-isoglutaminate (59573-84-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / 3.8N HCl / acetic acid; ethyl acetate / 2 h

2: 1.) N-methylmorpholine, isobutyl chloroformate, 2.) N-methylmorpholine / 1.) AcOEt, DMF, -25 deg C, 5 min, 2.) AcOEt, DMF, r.t.

With 4-methyl-morpholine; hydrogenchloride; isobutyl chloroformate; In acetic acid; ethyl acetate;

DOI:10.1002/hlca.19930760819

Reference yield:

benzyl (R)-5-amino-4-((tert-butoxycarbonyl)amino)-5-oxopentanoate (18800-73-2,19238-66-5) → benzyl N2-(N-acetyl-1-O-benzyl-4,6-O-benzylidene-α-D-muramoyl)-L-alanyl-D-isoglutaminate (59573-84-1)

Guidance literature:

Multi-step reaction with 4 steps

1: CF₃COOH / 0.25 h / Ambient temperature

2: acetonitrile / 15 h / Ambient temperature

3: CF₃COOH / 0.33 h / Ambient temperature

4: acetonitrile / 15 h / Ambient temperature

With trifluoroacetic acid; In acetonitrile;

DOI:10.1246/bcsj.53.2570

Reference yield:

N-(tert-butyloxycarbonyl)-γ-benzyl-D-glutamic acid (35793-73-8) → benzyl N2-(N-acetyl-1-O-benzyl-4,6-O-benzylidene-α-D-muramoyl)-L-alanyl-D-isoglutaminate (59573-84-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 86.8 percent / dicyclohexylcarbodiimide (DCC) / ethyl acetate / 2 h / 0 °C

2: 70.8 percent / 25percent aq. ammonia / tetrahydrofuran / 2 h / Ambient temperature

3: CF₃COOH / 0.25 h / Ambient temperature

4: acetonitrile / 15 h / Ambient temperature

5: CF₃COOH / 0.33 h / Ambient temperature

6: acetonitrile / 15 h / Ambient temperature

With ammonium hydroxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; ethyl acetate; acetonitrile;

DOI:10.1246/bcsj.53.2570

upstream raw materials:

L-alanyl-(γ-benzyl ester D-isoglutamine)

Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-<(R)-1-carboxyethyl>-α-D-glucopyranoside, HONB ester

L-alanyl-D-isoglutamine benzyl ester hydrochloride

Benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-<(R)-1-carboxyethyl>-α-D-glucopyranoside

Downstream raw materials:

benzyl (R)-4-((S)-2-((R)-2-(((2S,3R,4R,5S,6R)-3-acetamido-2-(benzyloxy)-5-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl)oxy)propanamido)propanamido)-5-amino-5-oxopentanoate

muramyl dipeptide

Refernces

• 1、 Fukuda,Kobayashi,Yukimasa,Imada,Fujino,Azuma,Yamamura. "Synthesis of immunologically active muramyl dipeptide derivatives containing a quinonyl moiety via aminoacyl intermediates". . p. 2215 - 2221. Retrieved 2007/10/02.
• 2、 Kusumoto,Tarumi,Ikenaka,Shiba. "Chemical synthesis of N acetylmuramyl peptides with partial structures of bacterial cell wall and their analogs in relation to immunoadjuvant activities". . p. 533 - 539. Retrieved 2007/10/07.