950170-55-5

Upstream product

• 864948-63-0 (+)-(1R,2R,3S,4R,5R,6S)-2-azido-3,4,5,6-tetrakisbenzyloxycyclohexanol 
• 124-63-0 methanesulfonyl chloride 
• 949887-64-3 (1R,2R,3S,6S)-6-(pivaloyloxy)cyclohex-4-ene-1,2,3-triyl triacetate 
• 110550-28-2 (+)-(1S,2R,3S,4S,5R,6R)-2,3,4,5-tetrakisbenzyloxy-7-oxabicyclo[4.1.0]heptane 
• 138258-55-6 (1S,2R,3R,4S)-1,2,3,4,tetrahydroxy-5-cyclohexene 
• 6090-95-5 (+)-(1R,2R,3S,4S,5R,6S)-2,3,4,5-tetraol-7-oxabicyclo[4.1.0]heptane 
• 4381-96-8 (+/-)-(1,3/2,4)-1,2,3,4-tetra-O-acetyl-5-cyclohexene-1,2,3,4-tetrol 

Downstream Products

• 949887-65-4 (+)-(1S,2R,3S,4R,5R,6S)-2-azido-3,4,5,6-tetrakisbenzyloxycyclohexanol 
• 949887-66-5 (-)-(1S,2R,3S,4R,5R,6S)-2-amino-3,4,5,6-tetrakisbenzyloxycyclohexanol 

Relevant academic research and scientific papers

Practical synthesis of (-)-1-amino-1-deoxy-myo-inositol from achiral precursors

A new synthesis of enantiomerically pure 1-amino-1-deoxy-myo-inositol is reported. The route described employs p-benzoquinone, an achiral compound, as the starting material to give conduritol B tetraacetate in three steps. Kinetic resolution of this compound using a palladium catalyst with a chiral ligand allows access to a conduritol B tetraester in high enantiomeric excess. This compound is transformed into tetrabenzyl conduritol B epoxide, which is regioselectively opened with azide to give the key azidocyclitol. Final transformation into (-)-1-amino-1-deoxy-myo-inositol hydrochloride is achieved in four synthetic steps. This sequence allows the synthesis of this compound in high enantiomeric purity in a semi-preparative scale.