((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

Base Information

• Chemical Name: ((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
• CAS No.: 220612-64-6
• Molecular Formula: C₅₈H₉₉N₅O₂₁S
• Molecular Weight: 1234.51
• Mol file: 220612-64-6.mol

Synonyms:((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

Chemical Property of ((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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((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

There total 4 articles about ((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 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: 72.0%

2,4,6-triisopropylphenylsulfonyl chloride (6553-96-4) + 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) → ((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)

Guidance literature:

With pyridine; at 20 ℃; for 36h;

DOI:10.1039/d0cc05031h

Reference yield: 31.0%

2,4,6-triisopropylphenylsulfonyl chloride (6553-96-4) + 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) → C73H121N5O23S2 (1477468-21-5) + C73H121N5O23S2 (1477468-22-6) + ((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)

Guidance literature:

With pyridine; at 23 ℃; for 96h; regioselective reaction; Inert atmosphere;

DOI:10.1021/ol4030138

Reference yield:

tobramycin (32986-56-4) → ((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)

Guidance literature:

Multi-step reaction with 2 steps

1: triethylamine / water; N,N-dimethyl-formamide / 55 °C

2: pyridine / 48 h / 20 °C

With pyridine; triethylamine; In water; N,N-dimethyl-formamide;

DOI:10.1002/cmdc.201200150

upstream raw materials:

2,4,6-triisopropylphenylsulfonyl chloride

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)

tobramycin

di-tert-butyl dicarbonate

Downstream raw materials:

6''-amino-6''-deoxy-(Boc)-5-tobramycin

6''-deoxy-6''-guanidino(Boc)7tobramycin

C₃₄H₆₈N₆O₉