4-nitrobenzyl ((2S,5R,6R)-6-((1R,2S,3S,4R,6S)-3-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-((methyl)tert-butoxycarbonylamino)tetrahydro-2H-pyran-2-yloxy)-6-(tert-butoxycarbonylamino)-2-hydroxy-4-((S)-2-hydroxy-4-(tert-butoxycarbonylamino)butanamido)cyclohexyloxy)-5-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-2-yl)methylcarbamate

Base Information

• Chemical Name: 4-nitrobenzyl ((2S,5R,6R)-6-((1R,2S,3S,4R,6S)-3-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-((methyl)tert-butoxycarbonylamino)tetrahydro-2H-pyran-2-yloxy)-6-(tert-butoxycarbonylamino)-2-hydroxy-4-((S)-2-hydroxy-4-(tert-butoxycarbonylamino)butanamido)cyclohexyloxy)-5-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-2-yl)methylcarbamate
• CAS No.: 1346507-61-6
• Molecular Formula: C₅₁H₈₃N₇O₂₁
• Molecular Weight: 1130.25

Synonyms:4-nitrobenzyl ((2S,5R,6R)-6-((1R,2S,3S,4R,6S)-3-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-((methyl)tert-butoxycarbonylamino)tetrahydro-2H-pyran-2-yloxy)-6-(tert-butoxycarbonylamino)-2-hydroxy-4-((S)-2-hydroxy-4-(tert-butoxycarbonylamino)butanamido)cyclohexyloxy)-5-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-2-yl)methylcarbamate

Chemical Property of 4-nitrobenzyl ((2S,5R,6R)-6-((1R,2S,3S,4R,6S)-3-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-((methyl)tert-butoxycarbonylamino)tetrahydro-2H-pyran-2-yloxy)-6-(tert-butoxycarbonylamino)-2-hydroxy-4-((S)-2-hydroxy-4-(tert-butoxycarbonylamino)butanamido)cyclohexyloxy)-5-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-2-yl)methylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-nitrobenzyl ((2S,5R,6R)-6-((1R,2S,3S,4R,6S)-3-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-((methyl)tert-butoxycarbonylamino)tetrahydro-2H-pyran-2-yloxy)-6-(tert-butoxycarbonylamino)-2-hydroxy-4-((S)-2-hydroxy-4-(tert-butoxycarbonylamino)butanamido)cyclohexyloxy)-5-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-2-yl)methylcarbamate

There total 7 articles about 4-nitrobenzyl ((2S,5R,6R)-6-((1R,2S,3S,4R,6S)-3-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-((methyl)tert-butoxycarbonylamino)tetrahydro-2H-pyran-2-yloxy)-6-(tert-butoxycarbonylamino)-2-hydroxy-4-((S)-2-hydroxy-4-(tert-butoxycarbonylamino)butanamido)cyclohexyloxy)-5-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-2-yl)methylcarbamate 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:

di-tert-butyl dicarbonate (24424-99-5) + C46H75N7O19 (1346507-60-5) → 4-nitrobenzyl ((2S,5R,6R)-6-((1R,2S,3S,4R,6S)-3-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-((methyl)tert-butoxycarbonylamino)tetrahydro-2H-pyran-2-yloxy)-6-(tert-butoxycarbonylamino)-2-hydroxy-4-((S)-2-hydroxy-4-(tert-butoxycarbonylamino)butanamido)cyclohexyloxy)-5-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-2-yl)methylcarbamate (1346507-61-6)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; at 20 ℃; for 18h;

Reference yield:

Gentamicin C1a (26098-04-4) → 4-nitrobenzyl ((2S,5R,6R)-6-((1R,2S,3S,4R,6S)-3-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-((methyl)tert-butoxycarbonylamino)tetrahydro-2H-pyran-2-yloxy)-6-(tert-butoxycarbonylamino)-2-hydroxy-4-((S)-2-hydroxy-4-(tert-butoxycarbonylamino)butanamido)cyclohexyloxy)-5-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-2-yl)methylcarbamate (1346507-61-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: zinc(II) acetate dihydrate / methanol / 18 h / 20 °C

1.2: 18 h / 20 °C

1.3: 0.5 h

2.1: zinc(II) acetate dihydrate / methanol / 18 h / 20 °C

2.2: 18 h / 20 °C

3.1: dimethyl sulfoxide / 1 h / 20 °C

4.1: 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide / tetrahydrofuran / 1.5 h / 20 °C

4.2: 18 h / 20 °C

4.3: 4 h

5.1: triethylamine / N,N-dimethyl-formamide / 18 h / 20 °C

With 1-hydroxy-pyrrolidine-2,5-dione; zinc(II) acetate dihydrate; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; dimethyl sulfoxide; N,N-dimethyl-formamide;

Reference yield:

(N-hydroxy-5-norbomene-2,3-dicarboxylimido)-4-nitrobenzyl carbonate (193269-82-8) → 4-nitrobenzyl ((2S,5R,6R)-6-((1R,2S,3S,4R,6S)-3-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-((methyl)tert-butoxycarbonylamino)tetrahydro-2H-pyran-2-yloxy)-6-(tert-butoxycarbonylamino)-2-hydroxy-4-((S)-2-hydroxy-4-(tert-butoxycarbonylamino)butanamido)cyclohexyloxy)-5-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-2-yl)methylcarbamate (1346507-61-6)

Guidance literature:

Multi-step reaction with 5 steps

1.1: zinc(II) acetate dihydrate / methanol / 18 h / 20 °C

1.2: 18 h / 20 °C

1.3: 0.5 h

2.1: zinc(II) acetate dihydrate / methanol / 18 h / 20 °C

2.2: 18 h / 20 °C

3.1: dimethyl sulfoxide / 1 h / 20 °C

4.1: 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide / tetrahydrofuran / 1.5 h / 20 °C

4.2: 18 h / 20 °C

4.3: 4 h

5.1: triethylamine / N,N-dimethyl-formamide / 18 h / 20 °C

With 1-hydroxy-pyrrolidine-2,5-dione; zinc(II) acetate dihydrate; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; dimethyl sulfoxide; N,N-dimethyl-formamide;

upstream raw materials:

di-tert-butyl dicarbonate

C₄₆H₇₅N₇O₁₉

Gentamicin C1a

(N-hydroxy-5-norbomene-2,3-dicarboxylimido)-4-nitrobenzyl carbonate

Downstream raw materials:

tert-butyl (2R,3R,6S)-6-(aminomethyl)-2-((1R,2S,3S,4R,6S)-3-((2R,3R,4R,5R)-4-((methyl)tert-butoxycarbonylamino)-3,5-dihydroxy-5-methyltetrahydro-2H-pyran-2-yloxy)-6-(tert-butoxycarbonylamino)-4-((S)-4-(tert-butoxycarbonylamino)-2-hydroxybutanamido)-2-hydroxycyclohexyloxy)tetrahydro-2H-pyran-3-ylcarbamate

2-(((2S,5R,6R)-5-(tert-butoxycarbonylamino)-6-((1R,2S,3S,4R,6S)-3-((2R,3R,4R,5R)-4-((methyl)tert-butoxycarbonylamino)-3,5-dihydroxy-5-methyltetrahydro-2H-pyran-2-yloxy)-6-(tert-butoxycarbonylamino)-4-((S)-4-(tert-butoxycarbonylamino)-2-hydroxybutanamido)-2-hydroxycyclohexyloxy)tetrahydro-2H-pyran-2-yl)methylamino)ethyl benzoate

tert-butyl (2R,3R,6S)-2-((1R,2S,3S,4R,6S)-3-((2R,3R,4R,5R)-4-((methyl)tert-butoxycarbonylamino)-3,5-dihydroxy-5-methyltetrahydro-2H-pyran-2-yloxy)-6-(tert-butoxycarbonylamino)-4-((S)-4-(tert-butoxycarbonylamino)-2-hydroxybutanamido)-2-hydroxycyclohexyloxy)-6-((2-hydroxyethylamino)methyl)tetrahydro-2H-pyran-3-ylcarbamate

(S)-4-amino-N-((1R,2S,3S,4R,5S)-5-amino-4-((2R,3R,6S)-3-amino-6-((2-hydroxyethylamino)methyl)tetrahydro-2H-pyran-2-yloxy)-2-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(methylamino)tetrahydro-2H-pyran-2-yloxy)-3-hydroxycyclohexyl)-2-hydroxy butanamide

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