(2R,3S,4R,5R,6S)-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-yl)oxy)-2-hydroxycyclohexyl)oxy)-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol

Base Information

• Chemical Name: (2R,3S,4R,5R,6S)-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-yl)oxy)-2-hydroxycyclohexyl)oxy)-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol
• CAS No.: 60618-90-8
• Molecular Formula: C₁₉H₃₈N₄O₁₀
• Molecular Weight: 482.532
• Mol file: 60618-90-8.mol

Synonyms:

Chemical Property of (2R,3S,4R,5R,6S)-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-yl)oxy)-2-hydroxycyclohexyl)oxy)-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4R,5R,6S)-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-yl)oxy)-2-hydroxycyclohexyl)oxy)-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol

There total 7 articles about (2R,3S,4R,5R,6S)-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-yl)oxy)-2-hydroxycyclohexyl)oxy)-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol 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:

gentamicin A (13291-74-2,55925-13-8) + S-adenosyl-L-methionine (485-80-3,15519-60-5,60018-85-1,60018-86-2,79845-28-6) → (2R,3S,4R,5R,6S)-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-yl)oxy)-2-hydroxycyclohexyl)oxy)-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol (36889-17-5,60618-89-5,60618-90-8,60618-92-0,60619-25-2) + 5'-deoxyadenosine (4754-39-6)

Guidance literature:

With sodium dithionite; methylcobalamin; ΔgenD1 mutant of methyltransferase GenD1; NADPH; diothiothreitol; In aq. buffer; at 30 ℃; for 12h; pH=8; Reagent/catalyst; Enzymatic reaction;

DOI:10.1016/j.chembiol.2014.12.012

Reference yield:

5,3′,4′,6′,2′′-penta-O-benzyl-1,3,2′-triazido-1,3,2′-tri(deamino)-3′′-N,4′′-O-carbonyl-gentamicin X2 → (2R,3S,4R,5R,6S)-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-yl)oxy)-2-hydroxycyclohexyl)oxy)-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol (36889-17-5,60618-89-5,60618-90-8,60618-92-0,60619-25-2)

Guidance literature:

5,3′,4′,6′,2′′-penta-O-benzyl-1,3,2′-triazido-1,3,2′-tri(deamino)-3′′-N,4′′-O-carbonyl-gentamicin X2; With 10% palladium hydroxide on charcoal; hydrogen; In 1,4-dioxane; water; for 36h; under 2068.65 Torr;

With water; barium(II) hydroxide; In 1,4-dioxane; at 60 ℃; for 12h; Inert atmosphere;

DOI:10.1021/acs.orglett.0c01107

Reference yield:

C57H66N6O16 → (2R,3S,4R,5R,6S)-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-yl)oxy)-2-hydroxycyclohexyl)oxy)-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol (36889-17-5,60618-89-5,60618-90-8,60618-92-0,60619-25-2)

Guidance literature:

With hydrogenchloride; hydrogen; palladium on activated charcoal; In 1,4-dioxane; acetic acid; for 48h; Yield given;

upstream raw materials:

Acetic acid (2R,3R,4R,5R)-4-(benzyloxycarbonyl-methyl-amino)-2-((1S,2S,3R,4S,6R)-4,6-bis-benzyloxycarbonylamino-2,3-dihydroxy-cyclohexyloxy)-5-hydroxy-5-methyl-tetrahydro-pyran-3-yl ester

gentamicin A

S-adenosyl-L-methionine