483341-79-3

Upstream product

• 301523-39-7 4-benzylamino-1,2,3,4,7,8-hexadeoxy-5,6-O-isopropylidene-D-ribo-oct-1,7-dienitol 
• 1694-92-4 2-Nitrobenzenesulfonyl chloride 
• 483341-78-2 (3R,4S,5S)-3,4-O-isopropylidene-5-(N-benzyl)-o-nitro-benzensulfon-amino-octa-1,7-diene-3,4-diol 

Downstream Products

• 688334-43-2 (1S,2R,6S)-6-(N-benzyl)-o-nitrobenzenesulfonamino-1,2-O-sulfonyl-cyclohex-3-ene-1,2-diol 
• 483341-81-7 (1R,4R,6S)-4,6-bis[(N-benzyl)-o-nitrobenzenesulfon-amino]-cyclohex-2-enol 
• 483341-80-6 (1S,2R,6S)-6-(N-benzyl)-o-nitrobenzenesulfonamino-1,2-di-O-carbonyl-cyclohex-3-ene-1,2-diol 
• 688334-35-2 (1S,2R,6S)-6-(N-benzyl)-o-nitrobenzenesulfonamino-cyclohex-3-ene-1,2-diol 

Relevant academic research and scientific papers

Synthesis of orthogonally protected 2-deoxystreptamine stereoisomers

Enantiomerically pure 4,6-diaminocyclohexenols are obtained from carbohydrate derived 1,7-dienes by ring-closing metathesis and palladium catalyzed allylic amination using o-nitrobenzenesulfonylamides as nucleophiles. In the latter reaction the use of a cyclic carbonate as a leaving group proved to be essential to facilitate a smooth substitution. The obtained compounds were converted into orthogonally protected diaminocyclitols, which are stereoisomers of the naturally occurring 2-deoxystreptamine, a constituent of aminoglycoside antibiotics.

A stereoselective route towards highly functionalized 4,6-diaminocyclohexene derivatives

A flexible synthetic route towards chirally pure 4,6-diaminocyclohexene derivatives based on palladium catalyzed allylic amination of carbohydrate derived cyclohexenes is presented.