N-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-Nα-(benzyloxycarbonyl)glycineamide

Base Information

• Chemical Name: N-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-Nα-(benzyloxycarbonyl)glycineamide
• CAS No.: 6216-47-3
• Molecular Formula: C₂₄H₃₁N₃O₁₁
• Molecular Weight: 537.524

Synonyms:N-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-Nα-(benzyloxycarbonyl)glycineamide

Chemical Property of N-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-Nα-(benzyloxycarbonyl)glycineamide

Chemical Property:

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Technology Process of N-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-Nα-(benzyloxycarbonyl)glycineamide

There total 10 articles about N-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-Nα-(benzyloxycarbonyl)glycineamide 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: 90.0%

2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosylamine (4515-24-6) + 2-(((benzyloxy)carbonyl)amino)ethanethioic S-acid (16707-70-3) → N-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-Nα-(benzyloxycarbonyl)glycineamide (6216-47-3)

Guidance literature:

With copper(II) acetate monohydrate; benzotriazol-1-ol; In water; N,N-dimethyl-formamide; at 20 ℃; for 0.5h; Reagent/catalyst; Solvent; Concentration; chemoselective reaction;

DOI:10.1021/ol302961s

Reference yield: 80.0%

2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosylamine (4515-24-6) + N-(Benzyloxycarbonyl)glycine (1138-80-3) → N-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-Nα-(benzyloxycarbonyl)glycineamide (6216-47-3)

Guidance literature:

With dicyclohexyl-carbodiimide; In tert-butyl alcohol; for 3h; Ambient temperature;

DOI:10.1016/0040-4039(95)00620-R

Reference yield: 71.0%

2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl azide (6205-69-2) + Z-Gly-SeH → N-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-Nα-(benzyloxycarbonyl)glycineamide (6216-47-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In chloroform; toluene; at 70 ℃; for 14h;

DOI:10.1021/ol047889z

upstream raw materials:

2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosylamine

N-(Benzyloxycarbonyl)glycine

2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl azide

2-(((benzyloxy)carbonyl)amino)ethanethioic S-acid

Downstream raw materials:

2-acetamido-1-N--2-deoxy-β-D-glycopyranosylamine

C₅₇H₈₇N₉O₁₈

C₅₃H₈₁N₇O₁₆

C₅₁H₈₁N₉O₁₅

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