O-3-deoxy-3-[[(1,1-dimethylethoxy)carbonyl]amino]-6-S-dodecyl-6-thio-α-D-glucopyranosyl-(1→6)-O-[2,3,6-trideoxy-2,6-bis[[(1,1-dimethylethoxy)carbonyl]amino]-α-D-ribo-hexopyranosyl-(1→4)]-2-deoxy-N¹,N³-bis[(1,1-dimethylethoxy)carbonyl]-D-streptamine

Base Information

• Chemical Name: O-3-deoxy-3-[[(1,1-dimethylethoxy)carbonyl]amino]-6-S-dodecyl-6-thio-α-D-glucopyranosyl-(1→6)-O-[2,3,6-trideoxy-2,6-bis[[(1,1-dimethylethoxy)carbonyl]amino]-α-D-ribo-hexopyranosyl-(1→4)]-2-deoxy-N¹,N³-bis[(1,1-dimethylethoxy)carbonyl]-D-streptamine
• CAS No.: 1392113-72-2
• Molecular Formula: C₅₅H₁₀₁N₅O₁₈S
• Molecular Weight: 1152.5

Synonyms:O-3-deoxy-3-[[(1,1-dimethylethoxy)carbonyl]amino]-6-S-dodecyl-6-thio-α-D-glucopyranosyl-(1→6)-O-[2,3,6-trideoxy-2,6-bis[[(1,1-dimethylethoxy)carbonyl]amino]-α-D-ribo-hexopyranosyl-(1→4)]-2-deoxy-N¹,N³-bis[(1,1-dimethylethoxy)carbonyl]-D-streptamine

Chemical Property of O-3-deoxy-3-[[(1,1-dimethylethoxy)carbonyl]amino]-6-S-dodecyl-6-thio-α-D-glucopyranosyl-(1→6)-O-[2,3,6-trideoxy-2,6-bis[[(1,1-dimethylethoxy)carbonyl]amino]-α-D-ribo-hexopyranosyl-(1→4)]-2-deoxy-N¹,N³-bis[(1,1-dimethylethoxy)carbonyl]-D-streptamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of O-3-deoxy-3-[[(1,1-dimethylethoxy)carbonyl]amino]-6-S-dodecyl-6-thio-α-D-glucopyranosyl-(1→6)-O-[2,3,6-trideoxy-2,6-bis[[(1,1-dimethylethoxy)carbonyl]amino]-α-D-ribo-hexopyranosyl-(1→4)]-2-deoxy-N¹,N³-bis[(1,1-dimethylethoxy)carbonyl]-D-streptamine

There total 3 articles about O-3-deoxy-3-[[(1,1-dimethylethoxy)carbonyl]amino]-6-S-dodecyl-6-thio-α-D-glucopyranosyl-(1→6)-O-[2,3,6-trideoxy-2,6-bis[[(1,1-dimethylethoxy)carbonyl]amino]-α-D-ribo-hexopyranosyl-(1→4)]-2-deoxy-N¹,N³-bis[(1,1-dimethylethoxy)carbonyl]-D-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: 92.0%

((2R,3S,4S,5R,6S)-6-(((1S,2S,3R,4S,6R)-4,6-bis((tert-butoxycarbonyl)amino)-3-(((2R,3R,5S,6R)-3-((tert-butoxycarbonyl)methyl)-5-hydroxytetrahydro-2Hpyran-2-yl)oxy)-2-hydroxycyclohexyl)oxy)-4-((tert-butoxycarbonyl)amino)-3,5-dihydroxytetrahydro-2H-pyran-2-yl)methyl 2,4,6-triisopropylbenzenesulfonate (220612-64-6) + 1-dodecylthiol (112-55-0) → O-3-deoxy-3-[[(1,1-dimethylethoxy)carbonyl]amino]-6-S-dodecyl-6-thio-α-D-glucopyranosyl-(1→6)-O-[2,3,6-trideoxy-2,6-bis[[(1,1-dimethylethoxy)carbonyl]amino]-α-D-ribo-hexopyranosyl-(1→4)]-2-deoxy-N1,N3-bis[(1,1-dimethylethoxy)carbonyl]-D-streptamine (1392113-72-2)

Guidance literature:

With caesium carbonate; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1002/anie.201200761

Reference yield:

tobramycin (32986-56-4) → O-3-deoxy-3-[[(1,1-dimethylethoxy)carbonyl]amino]-6-S-dodecyl-6-thio-α-D-glucopyranosyl-(1→6)-O-[2,3,6-trideoxy-2,6-bis[[(1,1-dimethylethoxy)carbonyl]amino]-α-D-ribo-hexopyranosyl-(1→4)]-2-deoxy-N1,N3-bis[(1,1-dimethylethoxy)carbonyl]-D-streptamine (1392113-72-2)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / water; dimethyl sulfoxide

2: pyridine

3: caesium carbonate / N,N-dimethyl-formamide / 20 °C

With pyridine; caesium carbonate; triethylamine; In water; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1002/anie.201200761

Reference yield:

di-tert-butyl ((1S,3R,4S,5S,6R)-4-(((2S,3R,4S,5S,6R)-4-((tert-butoxycarbonyl)amino)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-6-(((2R,3R,5S,6R)-3-((tert-butoxycarbonyl)amino)-6-(((tert-butoxycarbonyl)methyl)-5-hydroxytetrahydro-2H-pyran-2-yl)oxy)-5-hydroxycyclohexane-1,3-diyl)dicarbamate) (172950-21-9) → O-3-deoxy-3-[[(1,1-dimethylethoxy)carbonyl]amino]-6-S-dodecyl-6-thio-α-D-glucopyranosyl-(1→6)-O-[2,3,6-trideoxy-2,6-bis[[(1,1-dimethylethoxy)carbonyl]amino]-α-D-ribo-hexopyranosyl-(1→4)]-2-deoxy-N1,N3-bis[(1,1-dimethylethoxy)carbonyl]-D-streptamine (1392113-72-2)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine

2: caesium carbonate / N,N-dimethyl-formamide / 20 °C

With pyridine; caesium carbonate; In N,N-dimethyl-formamide;

DOI:10.1002/anie.201200761

upstream raw materials:

tobramycin

di-tert-butyl ((1S,3R,4S,5S,6R)-4-(((2S,3R,4S,5S,6R)-4-((tert-butoxycarbonyl)amino)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-6-(((2R,3R,5S,6R)-3-((tert-butoxycarbonyl)amino)-6-(((tert-butoxycarbonyl)methyl)-5-hydroxytetrahydro-2H-pyran-2-yl)oxy)-5-hydroxycyclohexane-1,3-diyl)dicarbamate)

((2R,3S,4S,5R,6S)-6-(((1S,2S,3R,4S,6R)-4,6-bis((tert-butoxycarbonyl)amino)-3-(((2R,3R,5S,6R)-3-((tert-butoxycarbonyl)methyl)-5-hydroxytetrahydro-2Hpyran-2-yl)oxy)-2-hydroxycyclohexyl)oxy)-4-((tert-butoxycarbonyl)amino)-3,5-dihydroxytetrahydro-2H-pyran-2-yl)methyl 2,4,6-triisopropylbenzenesulfonate

1-dodecylthiol

Downstream raw materials:

O-3-amino-3-deoxy-6-S-dodecyl-6-thio-α-D-glucopyranosyl-(1→6)-O-[2,6-diamino-2,3,6-trideoxy-α-D-ribo-hexopyranosyl-(1→4)]-2-deoxy-D-streptamine

C₃₀H₆₁N₅O₉S

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