N-phenyl-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) dichloroacetimidate

Base Information

• Chemical Name: N-phenyl-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) dichloroacetimidate
• CAS No.: 1228757-52-5
• Molecular Formula: C₂₂H₂₅Cl₂NO₁₀
• Molecular Weight: 534.347

Synonyms:N-phenyl-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) dichloroacetimidate

Chemical Property of N-phenyl-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) dichloroacetimidate

Chemical Property:

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Technology Process of N-phenyl-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) dichloroacetimidate

There total 2 articles about N-phenyl-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) dichloroacetimidate 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: 69.0%

2,3,4,5-tetra-O-acetyl-D-glucopyranose (3947-62-4,6207-76-7,19235-21-3,22554-70-7,22860-22-6,47339-09-3,57884-82-9,62057-79-8,70191-05-8,109525-54-4,140147-37-1,10343-06-3) + 2,2-dichloro-N-phenylacetimidoyl chloride (5512-78-7) → N-phenyl-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) dichloroacetimidate (1228757-52-5)

Guidance literature:

2,3,4,5-tetra-O-acetyl-D-glucopyranose; With 15-crown-5; sodium hydride; In dichloromethane; at 20 ℃; for 0.0833333h; Inert atmosphere;

2,2-dichloro-N-phenylacetimidoyl chloride; In dichloromethane; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1080/07328301003597673

Reference yield:

2,2,2-trichloro-N-phenylacetamide (2563-97-5) → N-phenyl-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) dichloroacetimidate (1228757-52-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triphenylphosphine / tetrachloromethane; dichloromethane / 4 h / 60 °C

2.1: 15-crown-5; sodium hydride / dichloromethane / 0.08 h / 20 °C / Inert atmosphere

2.2: 0.5 h / 20 °C / Inert atmosphere

With 15-crown-5; sodium hydride; triphenylphosphine; In tetrachloromethane; dichloromethane;

DOI:10.1080/07328301003597673

Reference yield: 71.0%

methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside (19488-48-3) + N-phenyl-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) dichloroacetimidate (1228757-52-5) → (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(((2R,3R,4S,5R,6S)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate (71692-91-6)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1080/07328301003597673

upstream raw materials:

2,3,4,5-tetra-O-acetyl-D-glucopyranose

2,2-dichloro-N-phenylacetimidoyl chloride

2,2,2-trichloro-N-phenylacetamide

Downstream raw materials:

(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(((2R,3R,4S,5R,6S)-4,5-bis(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran-3-yl)oxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate

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