O-2,6-dideoxy-2,6-bis<(trifluoroacetyl)amino>-3,4-bis-O-(p-nitrobenzoyl)-α-D-glucopyranosyl-(1->4)-O-<4,6-O-diacetyl-2,3-dideoxy-3-<(trifluoroacetyl)amino>-α-D-glucopyranosyl-(1->6)>-2-deoxy-1,3-bis-N-(trifluoroacetyl)-D-streptamine

Base Information

• Chemical Name: O-2,6-dideoxy-2,6-bis<(trifluoroacetyl)amino>-3,4-bis-O-(p-nitrobenzoyl)-α-D-glucopyranosyl-(1->4)-O-<4,6-O-diacetyl-2,3-dideoxy-3-<(trifluoroacetyl)amino>-α-D-glucopyranosyl-(1->6)>-2-deoxy-1,3-bis-N-(trifluoroacetyl)-D-streptamine
• CAS No.: 79633-99-1
• Molecular Formula: C₄₆H₄₂F₁₅N₇O₂₂
• Molecular Weight: 1329.85
• Mol file: 79633-99-1.mol

Synonyms:O-2,6-dideoxy-2,6-bis<(trifluoroacetyl)amino>-3,4-bis-O-(p-nitrobenzoyl)-α-D-glucopyranosyl-(1->4)-O-<4,6-O-diacetyl-2,3-dideoxy-3-<(trifluoroacetyl)amino>-α-D-glucopyranosyl-(1->6)>-2-deoxy-1,3-bis-N-(trifluoroacetyl)-D-streptamine

Chemical Property of O-2,6-dideoxy-2,6-bis<(trifluoroacetyl)amino>-3,4-bis-O-(p-nitrobenzoyl)-α-D-glucopyranosyl-(1->4)-O-<4,6-O-diacetyl-2,3-dideoxy-3-<(trifluoroacetyl)amino>-α-D-glucopyranosyl-(1->6)>-2-deoxy-1,3-bis-N-(trifluoroacetyl)-D-streptamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O-2,6-dideoxy-2,6-bis<(trifluoroacetyl)amino>-3,4-bis-O-(p-nitrobenzoyl)-α-D-glucopyranosyl-(1->4)-O-<4,6-O-diacetyl-2,3-dideoxy-3-<(trifluoroacetyl)amino>-α-D-glucopyranosyl-(1->6)>-2-deoxy-1,3-bis-N-(trifluoroacetyl)-D-streptamine

There total 9 articles about O-2,6-dideoxy-2,6-bis<(trifluoroacetyl)amino>-3,4-bis-O-(p-nitrobenzoyl)-α-D-glucopyranosyl-(1->4)-O-<4,6-O-diacetyl-2,3-dideoxy-3-<(trifluoroacetyl)amino>-α-D-glucopyranosyl-(1->6)>-2-deoxy-1,3-bis-N-(trifluoroacetyl)-D-streptamine 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: 38.4%

4,5-di-O-acetyl-1,2,3-trideoxy-3-<(trifluoroacetyl)amino>-D-arabino-hex-1-enopyranose (70333-69-6) + 3',4'-bis-O-(p-nitrobenzoyl)-1,2',3,6'-tetrakis-N-(trifluoroacetyl)neamine (61089-03-0) → O-2,6-dideoxy-2,6-bis<(trifluoroacetyl)amino>-3,4-bis-O-(p-nitrobenzoyl)-α-D-glucopyranosyl-(1->4)-O-<4,6-O-diacetyl-2,3-dideoxy-3-<(trifluoroacetyl)amino>-α-D-glucopyranosyl-(1->6)>-2-deoxy-1,3-bis-N-(trifluoroacetyl)-D-streptamine (79633-99-1)

Guidance literature:

With boron trifluoride diethyl etherate; In ethyl acetate; for 5h;

DOI:10.1021/jm00144a023

Reference yield:

neomycin A (3947-65-7) → O-2,6-dideoxy-2,6-bis<(trifluoroacetyl)amino>-3,4-bis-O-(p-nitrobenzoyl)-α-D-glucopyranosyl-(1->4)-O-<4,6-O-diacetyl-2,3-dideoxy-3-<(trifluoroacetyl)amino>-α-D-glucopyranosyl-(1->6)>-2-deoxy-1,3-bis-N-(trifluoroacetyl)-D-streptamine (79633-99-1)

Guidance literature:

Multi-step reaction with 5 steps

1: 75.3 percent / Et₃N / acetonitrile / 1 h / Ambient temperature

2: 76.3 percent / CF₃COOH / acetonitrile / 0.75 h / Heating

3: 94.2 percent / pyridine / 2.5 h / Ambient temperature

4: 80.7 percent / 66percent aq. HOAc / 4 h / 65 °C

5: 38.4 percent / BF₃*Et₂O / ethyl acetate / 5 h

With pyridine; boron trifluoride diethyl etherate; acetic acid; triethylamine; trifluoroacetic acid; In ethyl acetate; acetonitrile;

DOI:10.1021/jm00144a023

Reference yield:

1,2',3,6'-tetrakis-N-(trifluoroacetyl)neamine (61066-03-3) → O-2,6-dideoxy-2,6-bis<(trifluoroacetyl)amino>-3,4-bis-O-(p-nitrobenzoyl)-α-D-glucopyranosyl-(1->4)-O-<4,6-O-diacetyl-2,3-dideoxy-3-<(trifluoroacetyl)amino>-α-D-glucopyranosyl-(1->6)>-2-deoxy-1,3-bis-N-(trifluoroacetyl)-D-streptamine (79633-99-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 76.3 percent / CF₃COOH / acetonitrile / 0.75 h / Heating

2: 94.2 percent / pyridine / 2.5 h / Ambient temperature

3: 80.7 percent / 66percent aq. HOAc / 4 h / 65 °C

4: 38.4 percent / BF₃*Et₂O / ethyl acetate / 5 h

With pyridine; boron trifluoride diethyl etherate; acetic acid; trifluoroacetic acid; In ethyl acetate; acetonitrile;

DOI:10.1021/jm00144a023

upstream raw materials:

4,5-di-O-acetyl-1,2,3-trideoxy-3-<(trifluoroacetyl)amino>-D-arabino-hex-1-enopyranose

3',4'-bis-O-(p-nitrobenzoyl)-1,2',3,6'-tetrakis-N-(trifluoroacetyl)neamine

Acetic acid (2R,3S,4S,5R)-5,6-diacetoxy-2-acetoxymethyl-4-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-3-yl ester

neomycin A

Downstream raw materials:

2-deoxykanamycin B