949887-64-3

Upstream product

• 4381-96-8 (+/-)-(1,3/2,4)-1,2,3,4-tetra-O-acetyl-5-cyclohexene-1,2,3,4-tetrol 
• 75-98-9 Trimethylacetic acid 
• 3282-30-2 pivaloyl chloride 

Downstream Products

• 138258-55-6 (1S,2R,3R,4S)-1,2,3,4,tetrahydroxy-5-cyclohexene 
• 864948-63-0 (+)-(1R,2R,3S,4R,5R,6S)-2-azido-3,4,5,6-tetrakisbenzyloxycyclohexanol 
• 950170-55-5 (+)-(1R,2S,3S,4R,5S,6R)-(2-azido-3,4,5,6-tetrakisbenzyloxy)cyclohexyl methanesulfonate 
• 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 
• 6090-95-5 (+)-(1R,2R,3S,4S,5R,6S)-2,3,4,5-tetraol-7-oxabicyclo[4.1.0]heptane 
• 110550-28-2 (+)-(1S,2R,3S,4S,5R,6R)-2,3,4,5-tetrakisbenzyloxy-7-oxabicyclo[4.1.0]heptane 

Relevant academic research and scientific papers

Synthesis and evaluation of hydroxymethylaminocyclitols as glycosidase inhibitors

Four series of C7N aminocyclitol analogues of glucose were synthesized by stereocontrolled epoxide opening of hydroxyl protected forms of the cyclohexane epoxides cyclophellitol and 1,6-epi-cyclophellitol. The resulting hydroxymethyl substitute

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.

Pd catalyzed kinetic resolution of conduritol B. Asymmetric synthesis of (+)-cyclophellitol

Enantiomerically pure (+)-cyclophellitol is readily available from benzoquinone employing an asymmetric palladium catalyzed kinetic resolution of racemic conduritol B and a novel easily cleavable pivalate analogue.