(1S,4R,5S,8R)-2,6-(di-N-p-toluenesulphonyl)-2,6-diazabicyclo[3.2.1]octane-4,8-diol

Base Information

Chemical Name:(1S,4R,5S,8R)-2,6-(di-N-p-toluenesulphonyl)-2,6-diazabicyclo[3.2.1]octane-4,8-diol
CAS No.:1421610-56-1
Molecular Formula:C₂₀H₂₄N₂O₆S₂
Molecular Weight:452.552
Hs Code.:

Synonyms:(1S,4R,5S,8R)-2,6-(di-N-p-toluenesulphonyl)-2,6-diazabicyclo[3.2.1]octane-4,8-diol

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Chemical Property of (1S,4R,5S,8R)-2,6-(di-N-p-toluenesulphonyl)-2,6-diazabicyclo[3.2.1]octane-4,8-diol

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Technology Process of (1S,4R,5S,8R)-2,6-(di-N-p-toluenesulphonyl)-2,6-diazabicyclo[3.2.1]octane-4,8-diol

There total 3 articles about (1S,4R,5S,8R)-2,6-(di-N-p-toluenesulphonyl)-2,6-diazabicyclo[3.2.1]octane-4,8-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: 77.0%

: 1421610-55-0
(1S,4R,5S,8R)-4,8-di-O-benzoyl-2,6-(di-N-p-toluenesulphonyl)-2,6-diazabicyclo-[3.2.1]octane-4,8-diol

: 1421610-56-1
(1S,4R,5S,8R)-2,6-(di-N-p-toluenesulphonyl)-2,6-diazabicyclo[3.2.1]octane-4,8-diol

Guidance literature:: With sodium; In methanol; at 0 - 30 ℃;
DOI:10.1039/c2ob27000e

Reference yield:

: 1226778-54-6
3,4,6-tri-O-benzyl-1,2-dideoxy-1,2-(di-p-toluenesulfonamido)-D-glucitol

: 1421610-56-1
(1S,4R,5S,8R)-2,6-(di-N-p-toluenesulphonyl)-2,6-diazabicyclo[3.2.1]octane-4,8-diol

Guidance literature:: Multi-step reaction with 4 steps

1.1: triethylamine; dmap / dichloromethane / 0.17 h / Cooling with ice; Inert atmosphere

1.2: 3 h / 35 °C / Inert atmosphere

2.1: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 42 °C

3.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 3 h / 0 - 30 °C / Inert atmosphere

4.1: sodium / methanol / 0 - 30 °C

With dmap; palladium 10% on activated carbon; hydrogen; sodium; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; 3.1: |Mitsunobu Displacement;
DOI:10.1039/c2ob27000e

Reference yield:

: 1421610-50-5
5-O-benzoyl-3,4,6-tri-O-benzyl-1,2-dideoxy-1-N-benzoyl-1,2-(di-p-toluenesulfonamido)-D-glucitol

: 1421610-56-1
(1S,4R,5S,8R)-2,6-(di-N-p-toluenesulphonyl)-2,6-diazabicyclo[3.2.1]octane-4,8-diol

Guidance literature:: Multi-step reaction with 3 steps

1: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 42 °C

2: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 3 h / 0 - 30 °C / Inert atmosphere

3: sodium / methanol / 0 - 30 °C

With palladium 10% on activated carbon; hydrogen; sodium; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; 2: |Mitsunobu Displacement;
DOI:10.1039/c2ob27000e