N⁴-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-N²-(tert-butyloxycarbonyl)asparaginylphenylalanine 1,3-dithian-2ylmethyl ester

Base Information

• Chemical Name: N⁴-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-N²-(tert-butyloxycarbonyl)asparaginylphenylalanine 1,3-dithian-2ylmethyl ester
• CAS No.: 115652-08-9
• Molecular Formula: C₃₇H₅₂N₄O₁₄S₂
• Molecular Weight: 840.97

Synonyms:N⁴-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-N²-(tert-butyloxycarbonyl)asparaginylphenylalanine 1,3-dithian-2ylmethyl ester

Chemical Property of N⁴-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-N²-(tert-butyloxycarbonyl)asparaginylphenylalanine 1,3-dithian-2ylmethyl ester

Chemical Property:

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Technology Process of N⁴-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-N²-(tert-butyloxycarbonyl)asparaginylphenylalanine 1,3-dithian-2ylmethyl ester

There total 6 articles about N⁴-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-N²-(tert-butyloxycarbonyl)asparaginylphenylalanine 1,3-dithian-2ylmethyl ester 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: 86.0%

N-<2-(acetylamino)-2-deoxy-3,4,6-triacetyl-β-D-glucopyranosyl>-N2-<(1,1-dimethylethoxy)carbonyl>-L-asparagine (76521-35-2) + phenylalanine 1,3-dithian-2-ylmethyl ester (84010-54-8) → N4-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-N2-(tert-butyloxycarbonyl)asparaginylphenylalanine 1,3-dithian-2ylmethyl ester (115652-08-9)

Guidance literature:

With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; In dichloromethane; for 72h;

DOI:10.1021/jo00253a003

Reference yield:

methyl (2S)-2-amino-3-phenylpropanoate (2577-90-4) → N4-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-N2-(tert-butyloxycarbonyl)asparaginylphenylalanine 1,3-dithian-2ylmethyl ester (115652-08-9)

Guidance literature:

Multi-step reaction with 2 steps

1: Al(OiPr)3 / 4 h / 70 - 80 °C

2: 86 percent / trietylamine, ethyl 2-ethoxy-1,2-dihydroquinoline-1-carboxylate (EEDQ) / CH₂Cl₂ / 72 h

With aluminum isopropoxide; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; In dichloromethane;

DOI:10.1021/jo00253a003

Reference yield:

N-tert-Butyloxycarbonyl-L-asparaginsaeure-β-phenacylester (57680-14-5) → N4-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-N2-(tert-butyloxycarbonyl)asparaginylphenylalanine 1,3-dithian-2ylmethyl ester (115652-08-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) triethylamine, 2,4,6-trichlorobenzoyl chloride 2.) 4-(dimethylamino)pyridine / 1.) CH₂Cl₂, 2 h, 2.) 24 h, RT

2: 56 percent / sodium thiophenolate / dimethylformamide / 18 h / Ambient temperature

3: 74 percent / ethyl 2-ethoxy-1,2-dihydroquinoline-1-carboxylate (EEDQ) / CH₂Cl₂ / 18 h / Ambient temperature

4: 63 percent / 33percent aq. H₂O₂, (NH₄)2MoO₄ / acetone / 4 h / Ambient temperature

5: 86 percent / trietylamine, ethyl 2-ethoxy-1,2-dihydroquinoline-1-carboxylate (EEDQ) / CH₂Cl₂ / 72 h

With dmap; ammonium molibdate; 2,4,6-trichlorobenzoyl chloride; dihydrogen peroxide; sodium thiophenolate; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; In dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jo00253a003

upstream raw materials:

N-<2-(acetylamino)-2-deoxy-3,4,6-triacetyl-β-D-glucopyranosyl>-N²-<(1,1-dimethylethoxy)carbonyl>-L-asparagine

phenylalanine 1,3-dithian-2-ylmethyl ester

methyl (2S)-2-amino-3-phenylpropanoate

N-tert-Butyloxycarbonyl-L-asparaginsaeure-β-phenacylester

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