4-nitrobenzyl ((2S,5R,6R)-6-((1R,2R,3S,4R,6S)-4-amino-3-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(methylamino)tetrahydro-2H-pyran-2-yloxy)-6-(tert-butoxycarbonylamino)-2-hydroxycyclohexyloxy)-5-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-2-yl)methylcarbamate

Base Information

• Chemical Name: 4-nitrobenzyl ((2S,5R,6R)-6-((1R,2R,3S,4R,6S)-4-amino-3-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(methylamino)tetrahydro-2H-pyran-2-yloxy)-6-(tert-butoxycarbonylamino)-2-hydroxycyclohexyloxy)-5-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-2-yl)methylcarbamate
• CAS No.: 1346507-58-1
• Molecular Formula: C₃₇H₆₀N₆O₁₅
• Molecular Weight: 828.915
• Mol file: 1346507-58-1.mol

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

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

There total 3 articles about 4-nitrobenzyl ((2S,5R,6R)-6-((1R,2R,3S,4R,6S)-4-amino-3-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(methylamino)tetrahydro-2H-pyran-2-yloxy)-6-(tert-butoxycarbonylamino)-2-hydroxycyclohexyloxy)-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: 70.0%

di-tert-butyl dicarbonate (24424-99-5) + 4-nitrobenzyl ((2S,5R,6R)-5-amino-6-((1R,2S,3S,4R,6S)-4,6-diamino-3-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(methylamino)tetrahydro-2H-pyran-2-yloxy)-2-hydroxycyclohexyloxy)tetrahydro-2H-pyran-2-yl)methylcarbamate (1346507-57-0) → 4-nitrobenzyl ((2S,5R,6R)-6-((1R,2R,3S,4R,6S)-4-amino-3-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(methylamino)tetrahydro-2H-pyran-2-yloxy)-6-(tert-butoxycarbonylamino)-2-hydroxycyclohexyloxy)-5-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-2-yl)methylcarbamate (1346507-58-1)

Guidance literature:

4-nitrobenzyl ((2S,5R,6R)-5-amino-6-((1R,2S,3S,4R,6S)-4,6-diamino-3-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(methylamino)tetrahydro-2H-pyran-2-yloxy)-2-hydroxycyclohexyloxy)tetrahydro-2H-pyran-2-yl)methylcarbamate; With zinc(II) acetate dihydrate; In methanol; at 20 ℃; for 18h;

di-tert-butyl dicarbonate; dmap; In methanol; at 20 ℃; for 18h;

With ammonia; In ethanol;

Reference yield:

Gentamicin C1a (26098-04-4) → 4-nitrobenzyl ((2S,5R,6R)-6-((1R,2R,3S,4R,6S)-4-amino-3-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(methylamino)tetrahydro-2H-pyran-2-yloxy)-6-(tert-butoxycarbonylamino)-2-hydroxycyclohexyloxy)-5-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-2-yl)methylcarbamate (1346507-58-1)

Guidance literature:

Multi-step reaction with 2 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

With zinc(II) acetate dihydrate; In methanol;

Reference yield:

(N-hydroxy-5-norbomene-2,3-dicarboxylimido)-4-nitrobenzyl carbonate (193269-82-8) → 4-nitrobenzyl ((2S,5R,6R)-6-((1R,2R,3S,4R,6S)-4-amino-3-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(methylamino)tetrahydro-2H-pyran-2-yloxy)-6-(tert-butoxycarbonylamino)-2-hydroxycyclohexyloxy)-5-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-2-yl)methylcarbamate (1346507-58-1)

Guidance literature:

Multi-step reaction with 2 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

With zinc(II) acetate dihydrate; In methanol;

upstream raw materials:

di-tert-butyl dicarbonate

4-nitrobenzyl ((2S,5R,6R)-5-amino-6-((1R,2S,3S,4R,6S)-4,6-diamino-3-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(methylamino)tetrahydro-2H-pyran-2-yloxy)-2-hydroxycyclohexyloxy)tetrahydro-2H-pyran-2-yl)methylcarbamate

Gentamicin C1a

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

Downstream raw materials:

4-nitrobenzyl ((2S,5R,6R)-6-((1R,2R,3S,4R,6S)-4-amino-3-((2R,3R,4R,5R)-3,5-dihydroxy-5-methyl-4-(2,2,2-trifluoro-N-methylacetamido)tetrahydro-2H-pyran-2-yloxy)-6-(tert-butoxycarbonylamino)-2-hydroxycyclohexyloxy)-5-(tert-butoxycarbonylamino)tetrahydro-2H-pyran-2-yl)methylcarbamate

C₄₆H₇₅N₇O₁₉

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

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