1,6:2,3-dianhydro-4-O-(4,6-O-benzylidene-2-O-tosyl-α-D-glucopyranosyl)-β-D-mannopyranose

Base Information

• Chemical Name: 1,6:2,3-dianhydro-4-O-(4,6-O-benzylidene-2-O-tosyl-α-D-glucopyranosyl)-β-D-mannopyranose
• CAS No.: 78172-79-9
• Molecular Formula: C₂₆H₂₈O₁₁S
• Molecular Weight: 548.568

Synonyms:1,6:2,3-dianhydro-4-O-(4,6-O-benzylidene-2-O-tosyl-α-D-glucopyranosyl)-β-D-mannopyranose

Chemical Property of 1,6:2,3-dianhydro-4-O-(4,6-O-benzylidene-2-O-tosyl-α-D-glucopyranosyl)-β-D-mannopyranose

Chemical Property:

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Technology Process of 1,6:2,3-dianhydro-4-O-(4,6-O-benzylidene-2-O-tosyl-α-D-glucopyranosyl)-β-D-mannopyranose

There total 2 articles about 1,6:2,3-dianhydro-4-O-(4,6-O-benzylidene-2-O-tosyl-α-D-glucopyranosyl)-β-D-mannopyranose 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%

1,6-anhydro-4',6'-O-benzylidene-2,2'-di-O-tosyl-β-maltose (78101-89-0) → 1,6:2,3-dianhydro-4-O-(4,6-O-benzylidene-2-O-tosyl-α-D-glucopyranosyl)-β-D-mannopyranose (78172-79-9)

Guidance literature:

With sodium methylate; In methanol; Ambient temperature;

DOI:10.1248/cpb.29.421

Reference yield: 10.9%

1,6-anhydro-4',6'-O-benzylidene-β-maltose (56838-36-9) + p-toluenesulfonyl chloride (98-59-9) → 1,6:2,3-dianhydro-4-O-(4,6-O-benzylidene-2,3-di-O-tosyl-α-D-glucopyranosyl)-β-D-mannopyranose (87017-89-8) + 1,6-anhydro-4',6'-O-benzylidene-2,2'-di-O-tosyl-β-maltose (78101-89-0) + 1,6:2,3-dianhydro-4-O-(4,6-O-benzylidene-2-O-tosyl-α-D-glucopyranosyl)-β-D-mannopyranose (78172-79-9) + 1,6-anhydro-4',6'-O-benzylidene-2'-O-tosyl-β-maltose (78101-90-3)

Guidance literature:

With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; In dichloromethane; for 1.5h; Ambient temperature;

Reference yield: 85.1%

benzyl bromide (100-39-0) + 1,6:2,3-dianhydro-4-O-(4,6-O-benzylidene-2-O-tosyl-α-D-glucopyranosyl)-β-D-mannopyranose (78172-79-9) → 1,6:2,3-dianhydro-4-O-(3-O-benzyl-4,6-O-benzylidene-2-O-tosyl-α-D-glucopyranosyl)-β-D-mannopyranose (79636-23-0)

Guidance literature:

With barium dihydroxide; barium(II) oxide; In N,N-dimethyl-formamide; 0 deg C, 30 min, RT, 20 h;

DOI:10.1248/cpb.29.1893

upstream raw materials:

1,6-anhydro-4',6'-O-benzylidene-2,2'-di-O-tosyl-β-maltose

1,6-anhydro-4',6'-O-benzylidene-β-maltose

p-toluenesulfonyl chloride

Downstream raw materials:

1,6:2,3-dianhydro-4-O-(2,3-di-O-acetyl-4,6-O-benzylidene-α-D-glucopyranosyl)-β-D-mannopyranose

1,6:2,3-dianhydro-4-O-(3-O-benzyl-4,6-O-benzylidene-2-O-tosyl-α-D-glucopyranosyl)-β-D-mannopyranose

1,6:2,3-dianhydro-4-O-(2,3-anhydro-4,6-O-benzylidene-α-D-mannopyranosyl)-β-D-mannopyranose

1,6:2,3-dianhydro-4-O-(2-O-tosyl-α-D-glucopyranosyl)-β-D-mannopyranose

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