1,6-anhydro-4-O-benzyl-2,3-dideoxy-2,3-(N-o-nitrobenzenesulfonylepimino)-β-D-allopyranose

Base Information

• Chemical Name: 1,6-anhydro-4-O-benzyl-2,3-dideoxy-2,3-(N-o-nitrobenzenesulfonylepimino)-β-D-allopyranose
• CAS No.: 648858-48-4
• Molecular Formula: C₁₉H₁₈N₂O₇S
• Molecular Weight: 418.427

Synonyms:1,6-anhydro-4-O-benzyl-2,3-dideoxy-2,3-(N-o-nitrobenzenesulfonylepimino)-β-D-allopyranose

Chemical Property of 1,6-anhydro-4-O-benzyl-2,3-dideoxy-2,3-(N-o-nitrobenzenesulfonylepimino)-β-D-allopyranose

Chemical Property:

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Technology Process of 1,6-anhydro-4-O-benzyl-2,3-dideoxy-2,3-(N-o-nitrobenzenesulfonylepimino)-β-D-allopyranose

There total 2 articles about 1,6-anhydro-4-O-benzyl-2,3-dideoxy-2,3-(N-o-nitrobenzenesulfonylepimino)-β-D-allopyranose 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:

1,6-anhydro-4-O-benzyl-2,3-dideoxy-2,3-epimino-β-D-allopyranose (101024-16-2) + 2-Nitrobenzenesulfonyl chloride (1694-92-4) → 1,6-anhydro-4-O-benzyl-2,3-dideoxy-2,3-(N-o-nitrobenzenesulfonylepimino)-β-D-allopyranose (648858-48-4)

Guidance literature:

With triethylamine; In tetrahydrofuran; at -30 - -10 ℃; for 1h;

DOI:10.1016/j.carres.2003.07.003

Reference yield:

1,6-Anhydro-2-azido-4-O-benzyl-2-deoxy-3-O-tosyl-β-D-glucopyranose (359772-40-0) → 1,6-anhydro-4-O-benzyl-2,3-dideoxy-2,3-(N-o-nitrobenzenesulfonylepimino)-β-D-allopyranose (648858-48-4)

Guidance literature:

Multi-step reaction with 2 steps

1: NaBH₄ / tetrahydrofuran / 20 °C

2: 1.19 g / Et₃N / tetrahydrofuran / 1 h / -30 - -10 °C

With sodium tetrahydroborate; triethylamine; In tetrahydrofuran;

DOI:10.1016/j.carres.2003.07.003

Reference yield: 80.0%

4-amino-1,6-anhydro-2-O-benzyl-4-deoxy-β-D-glucopyranose (61784-07-4) + 1,6-anhydro-4-O-benzyl-2,3-dideoxy-2,3-(N-o-nitrobenzenesulfonylepimino)-β-D-allopyranose (648858-48-4) → 1,6-anhydro-3-(1,6-anhydro-2-O-benzyl-4-deoxy-β-D-glucopyranos-4-ylamino)-4-O-benzyl-2,3-dideoxy-2-(2-nitrobenzene-1-sulfonamido)-β-D-glucopyranose

Guidance literature:

With N-methylpyridinium p-toluenesulfonate; at 115 - 120 ℃; for 2h;

DOI:10.1016/j.carres.2006.11.028

upstream raw materials:

1,6-anhydro-4-O-benzyl-2,3-dideoxy-2,3-epimino-β-D-allopyranose

2-Nitrobenzenesulfonyl chloride

1,6-Anhydro-2-azido-4-O-benzyl-2-deoxy-3-O-tosyl-β-D-glucopyranose

Downstream raw materials:

1,6-anhydro-4-O-benzyl-3,4-dideoxy-3-fluoro-2-(N-2-nitrobenzene-1-sulfonamido)-β-D-glucopyranose

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