1,3,2’,6’-tetraazido-5,6,3’-tri-O-benzyl-4’-deoxy-4’-fluoro-4’-epineamine

Base Information

• Chemical Name: 1,3,2’,6’-tetraazido-5,6,3’-tri-O-benzyl-4’-deoxy-4’-fluoro-4’-epineamine
• CAS No.: 1624627-59-3
• Molecular Formula: C₃₃H₃₅FN₁₂O₅
• Molecular Weight: 698.717

Synonyms:1,3,2’,6’-tetraazido-5,6,3’-tri-O-benzyl-4’-deoxy-4’-fluoro-4’-epineamine

Chemical Property of 1,3,2’,6’-tetraazido-5,6,3’-tri-O-benzyl-4’-deoxy-4’-fluoro-4’-epineamine

Chemical Property:

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Technology Process of 1,3,2’,6’-tetraazido-5,6,3’-tri-O-benzyl-4’-deoxy-4’-fluoro-4’-epineamine

There total 8 articles about 1,3,2’,6’-tetraazido-5,6,3’-tri-O-benzyl-4’-deoxy-4’-fluoro-4’-epineamine 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: 32.0%

1,3,2’,6’-tetraazido-5,6,3’-tri-O-benzylneamine (1624627-58-2) → 1,3,2’,6’-tetraazido-5,6,3’-tri-O-benzyl-4’-deoxy-4’-fluoro-4’-epineamine (1624627-59-3) + 1,3,2’,6’-tetraazido-5,6,3’-tri-O-benzyl-4’-deoxy-4’-fluoroneamine (1624627-60-6)

Guidance literature:

With diethylamino-sulfur trifluoride; In dichloromethane; at 22 - 26 ℃; Inert atmosphere;

DOI:10.1039/c4md00072b

Reference yield:

1,3,2’,6’-tetraazido-5,6,3’-tri-O-benzyl-4’-O-trifluoromethanesulfonylneamine (1624627-62-8) → 1,3,2’,6’-tetraazido-5,6,3’-tri-O-benzyl-4’-deoxy-4’-fluoro-4’-epineamine (1624627-59-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 60 ℃; for 2h; Inert atmosphere;

DOI:10.1039/c4md00072b

Reference yield:

1,3,2’-triazido-5,6,3’-tri-O-benzyl-6’-O-(p-toluenesulfonyl)paromamine (1624627-57-1) → 1,3,2’,6’-tetraazido-5,6,3’-tri-O-benzyl-4’-deoxy-4’-fluoro-4’-epineamine (1624627-59-3)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium azide / N,N-dimethyl-formamide / 15 h / 70 °C / Inert atmosphere

2: diethylamino-sulfur trifluoride / dichloromethane / 22 - 26 °C / Inert atmosphere

With sodium azide; diethylamino-sulfur trifluoride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/c4md00072b

upstream raw materials:

(2R,3S,4R,5R,6S)-5-azido-6-(((1R,2R,3S,4R,6S)-4, 6-diazido-2,3-dihydroxycyclohexyl)oxy)-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol

1,3,2’-triazido-4’,6’-O-benzylideneparomamine

1,3,2’-triazido-5,6,3’-tri-O-benzyl-4’,6’-O-benzylidene paromamine

1,3,2’-triazido-5,6,3’-tri-O-benzyl paromamine

Downstream raw materials:

4’-deoxy-4’-fluoro-4’-epineamine

C₃₃H₄₃FN₄O₅

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