688334-52-3

Upstream product

• 688334-50-1 (1S,4S,6R)-4,6-bis[(N-benzyl)-o-nitrobenzenesulfon-amino]-1-O-(tert-butyldimethylsilyl)-cyclohex-2-enol 
• 483341-82-8 Benzyl-[(R)-1-((4R,5S)-2,2-dimethyl-5-vinyl-[1,3]dioxolan-4-yl)-but-3-enyl]-amine 
• 483341-85-1 (1R,2S,6R)-6-(N-benzyl)-o-nitrobenzenesulfonamino-1,2-di-O-carbonyl-cyclohex-3-ene-1,2-diol 
• 483341-84-0 (1R,2S,6R)-6-(N-benzyl)-o-nitrobenzenesulfonamino-1,2-O-isopropylidene-cyclohex-3-en-1,2-diol 
• 100-46-9 benzylamine 
• 1694-92-4 2-Nitrobenzenesulfonyl chloride 
• 42060-32-2 N-benzyl-2-nitrobenzenesulfonamide 

Downstream Products

• 688334-55-6 C₃₈H₄₆N₄O₁₁S₂SiCCH₂OCH₂ 

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.