methyl 2-amino-4,6-O-benzylidene-2-C-cyano-2,3-dideoxy-β-D-arabino-hexopyranoside

Base Information

• Chemical Name: methyl 2-amino-4,6-O-benzylidene-2-C-cyano-2,3-dideoxy-β-D-arabino-hexopyranoside
• CAS No.: 115984-09-3
• Molecular Formula: C₁₅H₁₈N₂O₄
• Molecular Weight: 290.319

Synonyms:methyl 2-amino-4,6-O-benzylidene-2-C-cyano-2,3-dideoxy-β-D-arabino-hexopyranoside

Chemical Property of methyl 2-amino-4,6-O-benzylidene-2-C-cyano-2,3-dideoxy-β-D-arabino-hexopyranoside

Chemical Property:

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Technology Process of methyl 2-amino-4,6-O-benzylidene-2-C-cyano-2,3-dideoxy-β-D-arabino-hexopyranoside

There total 2 articles about methyl 2-amino-4,6-O-benzylidene-2-C-cyano-2,3-dideoxy-β-D-arabino-hexopyranoside 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: 68.0%

Methyl-4,6-O-benzyliden-3-deoxy-α-D-erythro-hexo-pyranosid-2-ulose (19272-50-5) + trimethylsilyl cyanide (7677-24-9) → methyl 2-amino-4,6-O-benzylidene-2-C-cyano-2,3-dideoxy-α-D-ribo-hexopyranoside (115983-96-5,115983-97-6,115984-09-3)

Guidance literature:

With ammonia; In methanol; at 50 ℃; for 72h;

DOI:10.1021/jo00254a048

Reference yield: 57.0%

trimethylsilyl cyanide (7677-24-9) + methyl 4,6-O-benzylidene-3-deoxy-β-D-erythro-hexopyranozide-2-ulose (31505-12-1) → methyl 2-amino-4,6-O-benzylidene-2-C-cyano-2,3-dideoxy-β-D-ribo-hexopyranoside (115983-97-6) + methyl 2-amino-4,6-O-benzylidene-2-C-cyano-2,3-dideoxy-β-D-arabino-hexopyranoside (115984-09-3)

Guidance literature:

With ammonia; In methanol; for 120h;

DOI:10.1021/jo00254a048

Reference yield: 70.0%

methyl 2-amino-4,6-O-benzylidene-2-C-cyano-2,3-dideoxy-β-D-arabino-hexopyranoside (115984-09-3) + p-toluenesulfonyl chloride (98-59-9) → methyl 4,6-O-benzylidene-2-C-cyano-2,3-dideoxy-2-<(p-tolylsulfonyl)amino>-β-D-arabino-hexopyranoside (115983-98-7,115983-99-8)

Guidance literature:

With pyridine; Ambient temperature;

DOI:10.1021/jo00254a048

upstream raw materials:

Methyl-4,6-O-benzyliden-3-deoxy-α-D-erythro-hexo-pyranosid-2-ulose

trimethylsilyl cyanide

methyl 4,6-O-benzylidene-3-deoxy-β-D-erythro-hexopyranozide-2-ulose

Downstream raw materials:

methyl 4,6-O-benzylidene-2-C-cyano-2,3-dideoxy-2-<(p-tolylsulfonyl)amino>-α-D-ribo-hexopyranoside

methyl 2-C-(aminomethyl)-4,6-O-benzylidene-2,3-dideoxy-2-<(p-tolylsulfonyl)amino>-α-D-ribo-hexopyranoside

methyl 4,6-O-benzylidene-2,3-dideoxy-2-C-(hydroxymethyl)-2-<(p-tolylsulfonyl)amino>-α-D-ribo-hexopyranoside

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