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

Base Information

• Chemical Name: 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
• CAS No.: 1346507-64-9
• Molecular Formula: C₄₅H₈₂N₆O₁₈
• Molecular Weight: 995.175

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of 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

There total 9 articles about 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 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: 52.9%

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 (1346507-63-8) → 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 (1346507-64-9)

Guidance literature:

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; With water; sodium hydroxide; In methanol; at 20 ℃; for 0.5h;

With hydrogenchloride; In methanol; water; pH=7;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → 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 (1346507-64-9)

Guidance literature:

Multi-step reaction with 4 steps

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

2.1: sodium dithionite; water; sodium hydroxide / ethanol / 2 h / 70 °C

3.1: sodium cyanoborohydride; acetic acid / methanol / 3 h / 20 °C

4.1: water; sodium hydroxide / methanol / 0.5 h / 20 °C

4.2: pH 7

With sodium dithionite; water; sodium cyanoborohydride; acetic acid; triethylamine; sodium hydroxide; In methanol; ethanol; N,N-dimethyl-formamide;

Reference yield:

Gentamicin C1a (26098-04-4) → 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 (1346507-64-9)

Guidance literature:

Multi-step reaction with 8 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

6.1: sodium dithionite; water; sodium hydroxide / ethanol / 2 h / 70 °C

7.1: sodium cyanoborohydride; acetic acid / methanol / 3 h / 20 °C

8.1: water; sodium hydroxide / methanol / 0.5 h / 20 °C

8.2: pH 7

With 1-hydroxy-pyrrolidine-2,5-dione; sodium dithionite; water; zinc(II) acetate dihydrate; sodium cyanoborohydride; acetic acid; triethylamine; dicyclohexyl-carbodiimide; sodium hydroxide; In tetrahydrofuran; methanol; ethanol; dimethyl sulfoxide; N,N-dimethyl-formamide;

upstream raw materials:

Gentamicin C1a

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

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

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

Downstream raw materials:

(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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