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

Base Information

• Chemical Name: 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
• CAS No.: 128154-58-5
• Molecular Formula: C₄₃H₆₁N₇O₁₈
• Molecular Weight: 963.993

Synonyms: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

Chemical Property of 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

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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-asparaginyl-L-isoleucyl-L-serine allyl ester

There total 4 articles about 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 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: 81.0%

L-Isoleucyl-L-serine allyl ester hydrochloride (128154-43-8) + 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-asparaginyl-L-isoleucyl-L-serine allyl ester (128154-58-5)

Guidance literature:

With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; In chloroform;

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-asparaginyl-L-isoleucyl-L-serine allyl ester (128154-58-5)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 81 percent / EEDQ / CHCl₃

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:

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-asparaginyl-L-isoleucyl-L-serine allyl ester (128154-58-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 18 percent / Et₃N, EEDQ / CHCl₃ / 168 h / Ambient temperature

2: 81 percent / EEDQ / CHCl₃

With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; In chloroform;

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

upstream raw materials:

L-Isoleucyl-L-serine allyl ester hydrochloride

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

N-benzoylglycyl-L-threonine

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

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