N⁴-(2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-N²-(N-benzoylglycyl-L-threonyl)-L-asparagine allyl ester

Base Information

• Chemical Name: N⁴-(2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-N²-(N-benzoylglycyl-L-threonyl)-L-asparagine allyl ester
• CAS No.: 128154-53-0
• Molecular Formula: C₃₄H₄₅N₅O₁₅
• Molecular Weight: 763.756

Synonyms:N⁴-(2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-N²-(N-benzoylglycyl-L-threonyl)-L-asparagine allyl ester

Chemical Property of N⁴-(2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-N²-(N-benzoylglycyl-L-threonyl)-L-asparagine allyl 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-(N-benzoylglycyl-L-threonyl)-L-asparagine allyl ester

There total 2 articles about N⁴-(2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-N²-(N-benzoylglycyl-L-threonyl)-L-asparagine allyl 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: 51.0%

N-benzoylglycyl-L-threonine (117800-68-7) + N4-(2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-N2-L-asparagine allyl ester hydrochloride (118398-56-4) → N4-(2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-N2-(N-benzoylglycyl-L-threonyl)-L-asparagine allyl ester (128154-53-0)

Guidance literature:

With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In dichloromethane; for 168h; Ambient temperature;

DOI:10.1016/0008-6215(90)84107-6

Reference yield:

N4-(2-Acetamino-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-N2-(tert-butoxycarbonyl)-asparagin-allylester (88224-28-6) → N4-(2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-N2-(N-benzoylglycyl-L-threonyl)-L-asparagine allyl ester (128154-53-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / HCl / CH₂Cl₂; diethyl ether / 3 h / Ambient temperature

2: 18 percent / Et₃N, EEDQ / CHCl₃ / 168 h / Ambient temperature

With hydrogenchloride; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; In diethyl ether; dichloromethane; chloroform;

DOI:10.1016/0008-6215(90)84107-6

Reference yield: 93.0%

N4-(2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-N2-(N-benzoylglycyl-L-threonyl)-L-asparagine allyl ester (128154-53-0) → N4-(2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-N2-(N-benzoylglycyl-L-threonyl)-L-asparagine (128154-56-3)

Guidance literature:

Wilkinson's catalyst; In ethanol; water; at 70 ℃; for 24h;

DOI:10.1016/0008-6215(90)84107-6

upstream raw materials:

N-benzoylglycyl-L-threonine

N⁴-(2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-N²-L-asparagine allyl ester hydrochloride

N⁴-(2-Acetamino-3,4,6-tri-O-acetyl-2-desoxy-β-D-glucopyranosyl)-N²-(tert-butoxycarbonyl)-asparagin-allylester

Downstream raw materials:

N⁴-(2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-N²-(N-benzoylglycyl-L-threonyl)-L-asparaginyl-L-isoleucyl-L-serine allyl ester

N⁴-(2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-N²-(N-benzoylglycyl-L-threonyl)-L-asparagine

N⁴-(2-Acetamido-2-deoxy-β-D-glucopyranosyl)-N²-(N-benzoylglycyl-L-threonyl)-L-asparaginyl-L-isoleucyl-L-serine amide

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