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

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
• CAS No.: 128154-56-3
• Molecular Formula: C₃₁H₄₁N₅O₁₅
• Molecular Weight: 723.691

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

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

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

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-asparagine 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: 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

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 (128154-56-3)

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: 93 percent / tris(triphenylphosphine)rhodium(I) chloride / ethanol; H₂O / 24 h / 70 °C

With hydrogenchloride; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; Wilkinson's catalyst; In diethyl ether; ethanol; dichloromethane; chloroform; water;

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-asparagine (128154-56-3)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 93 percent / tris(triphenylphosphine)rhodium(I) chloride / ethanol; H₂O / 24 h / 70 °C

With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; Wilkinson's catalyst; In ethanol; chloroform; water;

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

upstream raw materials:

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

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

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