5-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl-(1<*>4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-1,3,2',6'-tetraazido-6,3',4'-tri-O-benzyl neamine

Base Information

• Chemical Name: 5-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl-(1<*>4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-1,3,2',6'-tetraazido-6,3',4'-tri-O-benzyl neamine
• CAS No.: 485810-22-8
• Molecular Formula: C₅₉H₇₀N₁₂O₂₃
• Molecular Weight: 1315.27
• Mol file: 485810-22-8.mol

Synonyms:5-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl-(1<*>4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-1,3,2',6'-tetraazido-6,3',4'-tri-O-benzyl neamine

Chemical Property of 5-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl-(1<*>4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-1,3,2',6'-tetraazido-6,3',4'-tri-O-benzyl neamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl-(1<*>4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-1,3,2',6'-tetraazido-6,3',4'-tri-O-benzyl neamine

There total 2 articles about 5-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl-(1<*>4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-1,3,2',6'-tetraazido-6,3',4'-tri-O-benzyl neamine 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: 60.0%

(1R,2R,5R,6S)-3,5-Diazido-2-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-6-benzyloxy-cyclohexanol + 4-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl trichloracetimidate (92052-38-5,106256-81-9,106256-89-7,126736-02-5,132287-70-8,132287-71-9,139403-73-9,130703-21-8) → 5-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl-(1<*>4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-1,3,2',6'-tetraazido-6,3',4'-tri-O-benzyl neamine (485810-22-8)

Guidance literature:

(1R,2R,5R,6S)-3,5-Diazido-2-((2R,3R,4R,5R,6R)-3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-6-benzyloxy-cyclohexanol; 4-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl trichloracetimidate; With 4 A molecular sieve; In dichloromethane; at 20 ℃; for 1h;

With boron trifluoride diethyl etherate; In dichloromethane; at -50 ℃; Further stages.;

DOI:10.1021/ol0269042

Reference yield:

α-D-cellobiose octaacetate (5346-90-7) → 5-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl-(1<*>4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-1,3,2',6'-tetraazido-6,3',4'-tri-O-benzyl neamine (485810-22-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: hydrazine acetate / dimethylformamide / 20 °C

1.2: 44 percent / DBU / CH₂Cl₂ / 20 °C

2.1: 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / 20 °C

2.2: 60 percent / BF₃*OEt₂ / CH₂Cl₂ / -50 °C

With 4 A molecular sieve; hydrazinium monoacetate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol0269042

Reference yield:

5-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl-(1<*>4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-1,3,2',6'-tetraazido-6,3',4'-tri-O-benzyl neamine (485810-22-8) → 2-{6-[3,5-diazido-2-(3-azido-6-azidomethyl-4,5-bis-benzyloxy-tetrahydro-pyran-2-yloxy)-6-benzyloxy-cyclohexyloxy]-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy}-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃;

DOI:10.1021/ol0269042

upstream raw materials:

4-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl trichloracetimidate

α-D-cellobiose octaacetate