4,6-O-benzylidene-1,2-ethylidene-3-O-(2',3',4',6'-tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranoside

Base Information

• Chemical Name: 4,6-O-benzylidene-1,2-ethylidene-3-O-(2',3',4',6'-tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranoside
• CAS No.: 868663-78-9
• Molecular Formula: C₂₉H₃₆O₁₅
• Molecular Weight: 624.596

Synonyms:4,6-O-benzylidene-1,2-ethylidene-3-O-(2',3',4',6'-tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranoside

Chemical Property of 4,6-O-benzylidene-1,2-ethylidene-3-O-(2',3',4',6'-tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranoside

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Technology Process of 4,6-O-benzylidene-1,2-ethylidene-3-O-(2',3',4',6'-tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranoside

There total 5 articles about 4,6-O-benzylidene-1,2-ethylidene-3-O-(2',3',4',6'-tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranoside 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: 66.0%

4,6-O-Benzylidene-1,2-O-ethylidene-β-D-mannopyranose (324041-33-0) + acetobromomannose (13242-53-0) → 4,6-O-benzylidene-1,2-ethylidene-3-O-(2',3',4',6'-tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranoside (868663-78-9)

Guidance literature:

With 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; at -20 ℃; for 2.66667h;

DOI:10.1016/j.tet.2005.01.090

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → 4,6-O-benzylidene-1,2-ethylidene-3-O-(2',3',4',6'-tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranoside (868663-78-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 5.08 g / (+)-10-camphorsulfonic acid / dimethylformamide / 6 h / 30 °C

2: 66 percent / AgOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / 2.67 h / -20 °C

With 4 A molecular sieve; silver trifluoromethanesulfonate; (+)-10-camphorsulfonic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2005.01.090

Reference yield:

1,2-O-ethylidene-(R,S)-β-D-mannopyranose (230953-16-9) → 4,6-O-benzylidene-1,2-ethylidene-3-O-(2',3',4',6'-tetra-O-acetyl-α-D-mannopyranosyl)-β-D-mannopyranoside (868663-78-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 5.08 g / (+)-10-camphorsulfonic acid / dimethylformamide / 6 h / 30 °C

2: 66 percent / AgOTf; 4 Angstroem molecular sieves / CH₂Cl₂ / 2.67 h / -20 °C

With 4 A molecular sieve; silver trifluoromethanesulfonate; (+)-10-camphorsulfonic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2005.01.090

upstream raw materials:

4,6-O-Benzylidene-1,2-O-ethylidene-β-D-mannopyranose

acetobromomannose

benzaldehyde dimethyl acetal

1,2-O-ethylidene-(R,S)-β-D-mannopyranose

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