bis[2-(α-D-mannopyranosyloxy)phenyl]buta-1,3-diyne

Base Information

• Chemical Name: bis[2-(α-D-mannopyranosyloxy)phenyl]buta-1,3-diyne
• CAS No.: 871311-16-9
• Molecular Formula: C₂₈H₃₀O₁₂
• Molecular Weight: 558.539

Synonyms:bis[2-(α-D-mannopyranosyloxy)phenyl]buta-1,3-diyne

Chemical Property of bis[2-(α-D-mannopyranosyloxy)phenyl]buta-1,3-diyne

Chemical Property:

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Technology Process of bis[2-(α-D-mannopyranosyloxy)phenyl]buta-1,3-diyne

There total 4 articles about bis[2-(α-D-mannopyranosyloxy)phenyl]buta-1,3-diyne 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: 100.0%

bis[2-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl]buta-1,3-diyne (1318797-56-6) → bis[2-(α-D-mannopyranosyloxy)phenyl]buta-1,3-diyne (871311-16-9)

Guidance literature:

bis[2-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl]buta-1,3-diyne; With sodium methylate; In methanol; at 20 ℃; for 14h; pH=8 - 9; Inert atmosphere;

In methanol;

DOI:10.1016/j.carres.2011.03.041

Reference yield:

2-iodophenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside (871311-11-4) → bis[2-(α-D-mannopyranosyloxy)phenyl]buta-1,3-diyne (871311-16-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / triethylamine; N,N-dimethyl-formamide / 60 °C / Inert atmosphere

2.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

3.1: copper diacetate / pyridine / 24 h / Inert atmosphere; Reflux

4.1: sodium methylate / methanol / 14 h / 20 °C / pH 8 - 9 / Inert atmosphere

4.2: amberlyst IR-120

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; sodium methylate; copper diacetate; acetic acid; In tetrahydrofuran; pyridine; methanol; triethylamine; N,N-dimethyl-formamide; 1.1: Sonogashira coupling / 3.1: Glaser coupling;

DOI:10.1016/j.carres.2011.03.041

Reference yield:

2-ethynylphenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside (871311-12-5) → bis[2-(α-D-mannopyranosyloxy)phenyl]buta-1,3-diyne (871311-16-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: copper diacetate / pyridine / 24 h / Inert atmosphere; Reflux

2.1: sodium methylate / methanol / 14 h / 20 °C / pH 8 - 9 / Inert atmosphere

2.2: amberlyst IR-120

With sodium methylate; copper diacetate; In pyridine; methanol; 1.1: Glaser coupling;

DOI:10.1016/j.carres.2011.03.041

upstream raw materials:

2-iodophenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside

2-ethynylphenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside

bis[2-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl]buta-1,3-diyne

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