N,N'-bis-benzyloxycarbonyl-O⁴-(3-benzyloxycarbonylamino-α-D-3-deoxy-glucopyranosyl)-O⁶-(2,6-bis-benzyloxycarbonylamino-α-D-2,6-dideoxy-glucopyranosyl)-1L-2-deoxy-streptamine

Base Information

• Chemical Name: N,N'-bis-benzyloxycarbonyl-O⁴-(3-benzyloxycarbonylamino-α-D-3-deoxy-glucopyranosyl)-O⁶-(2,6-bis-benzyloxycarbonylamino-α-D-2,6-dideoxy-glucopyranosyl)-1L-2-deoxy-streptamine
• CAS No.: 65269-36-5
• Molecular Formula: C₅₈H₆₇N₅O₂₀
• Molecular Weight: 1154.19

Synonyms:

Chemical Property of N,N'-bis-benzyloxycarbonyl-O⁴-(3-benzyloxycarbonylamino-α-D-3-deoxy-glucopyranosyl)-O⁶-(2,6-bis-benzyloxycarbonylamino-α-D-2,6-dideoxy-glucopyranosyl)-1L-2-deoxy-streptamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N,N'-bis-benzyloxycarbonyl-O⁴-(3-benzyloxycarbonylamino-α-D-3-deoxy-glucopyranosyl)-O⁶-(2,6-bis-benzyloxycarbonylamino-α-D-2,6-dideoxy-glucopyranosyl)-1L-2-deoxy-streptamine

There total 1 articles about N,N'-bis-benzyloxycarbonyl-O⁴-(3-benzyloxycarbonylamino-α-D-3-deoxy-glucopyranosyl)-O⁶-(2,6-bis-benzyloxycarbonylamino-α-D-2,6-dideoxy-glucopyranosyl)-1L-2-deoxy-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:

benzyl chloroformate (501-53-1,94274-21-2) + kananmycin B (4696-76-8) → N,N'-bis-benzyloxycarbonyl-O4-(3-benzyloxycarbonylamino-α-D-3-deoxy-glucopyranosyl)-O6-(2,6-bis-benzyloxycarbonylamino-α-D-2,6-dideoxy-glucopyranosyl)-1L-2-deoxy-streptamine (65269-36-5)

Guidance literature:

With sodium carbonate; In water; Yield given;

DOI:10.1016/S0040-4039(00)71171-3

Reference yield:

N,N'-bis-benzyloxycarbonyl-O4-(3-benzyloxycarbonylamino-α-D-3-deoxy-glucopyranosyl)-O6-(2,6-bis-benzyloxycarbonylamino-α-D-2,6-dideoxy-glucopyranosyl)-1L-2-deoxy-streptamine (65269-36-5) → 1-N-(1,3-dihydroxy-2-propyl)kanamycin B (66887-96-5)

Guidance literature:

Multi-step reaction with 6 steps

1: pyridine / 24 h / Ambient temperature

2: H₂, CH₃COOH / Pd-C (5 percent) / tetrahydrofuran; H₂O / 50 °C / 2585.7 Torr

3: aq. NH₃ / H₂O / 24 h / Ambient temperature

4: tetrahydrofuran; H₂O

5: sodium cyanoborohydride / methanol; H₂O

6: aq. caustic solution / H₂O

With ammonium hydroxide; caustic solution; hydrogen; sodium cyanoborohydride; acetic acid; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; water;

DOI:10.1016/S0040-4039(00)71171-3

Reference yield:

N,N'-bis-benzyloxycarbonyl-O4-(3-benzyloxycarbonylamino-α-D-3-deoxy-glucopyranosyl)-O6-(2,6-bis-benzyloxycarbonylamino-α-D-2,6-dideoxy-glucopyranosyl)-1L-2-deoxy-streptamine (65269-36-5) → 3-N-formyl-2',3'',6'-tri-N-acetylkanamycin B (70551-02-9)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridine / 24 h / Ambient temperature

2: H₂, CH₃COOH / Pd-C (5 percent) / tetrahydrofuran; H₂O / 50 °C / 2585.7 Torr

3: aq. NH₃ / H₂O / 24 h / Ambient temperature

4: tetrahydrofuran; H₂O

With ammonium hydroxide; hydrogen; acetic acid; palladium on activated charcoal; In tetrahydrofuran; pyridine; water;

DOI:10.1016/S0040-4039(00)71171-3

upstream raw materials:

benzyl chloroformate

kananmycin B

Downstream raw materials:

O⁴-(6-amino-2-benzyloxycarbonylamino-N⁶,O⁴-carbonyl-α-D-2,6-dideoxy-glucopyranosyl)-O⁶-(3-amino-N,O²-carbonyl-α-D-3-deoxy-glucopyranosyl)-N,N'-bis-benzyloxycarbonyl-1D-2-deoxy-streptamine

1-N-(1,3-dihydroxy-2-propyl)kanamycin B

2',3'',6'-tri-N-acetylkanamycin B

3-N-formyl-2',3'',6'-tri-N-acetylkanamycin B

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