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

Base Information

• Chemical Name: di-tert-butyl (((1S,3R,4S,5S,6R)-4-(((2R,3R,4S,5S,6R)-6-(azidomethyl)-4-((tertbutoxycarbonyl)amino)-3,5-dihydroxytetrahydro-2H-pyran-2-yl)oxy)-6-(((2R,3R,5S,6R)-3-((tert-butoxycarbonyl)amino)-methyl)-5-hydroxytetrahydro-2H-pyran-2-yl)oxy)-5-hydroxycyclohexane-1,3-diyl)dicarbamate
• CAS No.: 519171-28-9
• Molecular Formula: C₄₃H₇₆N₈O₁₈
• Molecular Weight: 993.119
• Mol file: 519171-28-9.mol

Synonyms:di-tert-butyl (((1S,3R,4S,5S,6R)-4-(((2R,3R,4S,5S,6R)-6-(azidomethyl)-4-((tertbutoxycarbonyl)amino)-3,5-dihydroxytetrahydro-2H-pyran-2-yl)oxy)-6-(((2R,3R,5S,6R)-3-((tert-butoxycarbonyl)amino)-methyl)-5-hydroxytetrahydro-2H-pyran-2-yl)oxy)-5-hydroxycyclohexane-1,3-diyl)dicarbamate

Chemical Property of di-tert-butyl (((1S,3R,4S,5S,6R)-4-(((2R,3R,4S,5S,6R)-6-(azidomethyl)-4-((tertbutoxycarbonyl)amino)-3,5-dihydroxytetrahydro-2H-pyran-2-yl)oxy)-6-(((2R,3R,5S,6R)-3-((tert-butoxycarbonyl)amino)-methyl)-5-hydroxytetrahydro-2H-pyran-2-yl)oxy)-5-hydroxycyclohexane-1,3-diyl)dicarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of di-tert-butyl (((1S,3R,4S,5S,6R)-4-(((2R,3R,4S,5S,6R)-6-(azidomethyl)-4-((tertbutoxycarbonyl)amino)-3,5-dihydroxytetrahydro-2H-pyran-2-yl)oxy)-6-(((2R,3R,5S,6R)-3-((tert-butoxycarbonyl)amino)-methyl)-5-hydroxytetrahydro-2H-pyran-2-yl)oxy)-5-hydroxycyclohexane-1,3-diyl)dicarbamate

There total 3 articles about di-tert-butyl (((1S,3R,4S,5S,6R)-4-(((2R,3R,4S,5S,6R)-6-(azidomethyl)-4-((tertbutoxycarbonyl)amino)-3,5-dihydroxytetrahydro-2H-pyran-2-yl)oxy)-6-(((2R,3R,5S,6R)-3-((tert-butoxycarbonyl)amino)-methyl)-5-hydroxytetrahydro-2H-pyran-2-yl)oxy)-5-hydroxycyclohexane-1,3-diyl)dicarbamate 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: 99.0%

tosyl-Boc5-tobramycin (194785-92-7) → di-tert-butyl (((1S,3R,4S,5S,6R)-4-(((2R,3R,4S,5S,6R)-6-(azidomethyl)-4-((tertbutoxycarbonyl)amino)-3,5-dihydroxytetrahydro-2H-pyran-2-yl)oxy)-6-(((2R,3R,5S,6R)-3-((tert-butoxycarbonyl)amino)-methyl)-5-hydroxytetrahydro-2H-pyran-2-yl)oxy)-5-hydroxycyclohexane-1,3-diyl)dicarbamate (519171-28-9)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 80 ℃; for 12h; Inert atmosphere;

Reference yield: 91.0%

((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) → di-tert-butyl (((1S,3R,4S,5S,6R)-4-(((2R,3R,4S,5S,6R)-6-(azidomethyl)-4-((tertbutoxycarbonyl)amino)-3,5-dihydroxytetrahydro-2H-pyran-2-yl)oxy)-6-(((2R,3R,5S,6R)-3-((tert-butoxycarbonyl)amino)-methyl)-5-hydroxytetrahydro-2H-pyran-2-yl)oxy)-5-hydroxycyclohexane-1,3-diyl)dicarbamate (519171-28-9)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 60 ℃; for 12h;

DOI:10.1039/c2md20162c

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) → di-tert-butyl (((1S,3R,4S,5S,6R)-4-(((2R,3R,4S,5S,6R)-6-(azidomethyl)-4-((tertbutoxycarbonyl)amino)-3,5-dihydroxytetrahydro-2H-pyran-2-yl)oxy)-6-(((2R,3R,5S,6R)-3-((tert-butoxycarbonyl)amino)-methyl)-5-hydroxytetrahydro-2H-pyran-2-yl)oxy)-5-hydroxycyclohexane-1,3-diyl)dicarbamate (519171-28-9)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 36 h / 20 °C

2: sodium azide / N,N-dimethyl-formamide / 24 h / 65 °C

With pyridine; sodium azide; In N,N-dimethyl-formamide;

DOI:10.1039/d0cc05031h

upstream raw materials:

((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

tosyl-Boc₅-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)