165375-20-2

Upstream product

• 17510-52-0 sodium chloro(ethoxycarbonyl)chloroamide 
• 80675-64-5 (3R,4R,5R)-3,4-dibenzoyloxy-5-(hydroxymethyl)cyclopent-1-ene 

Downstream Products

• 138395-78-5 (3aR,4R,5R,6R,6aS)-4,5-Dihydroxy-6-hydroxymethyl-hexahydro-cyclopentaoxazol-2-one 
• 165375-29-1 (1S,5R)-6-exo,7-endo-dibenzoyloxy-8-exo-hydroxymethyl-2-oxa-4-azabicyclo<3.3.0>octan-3-one 
• 158528-74-6 (1S,5S)-3-dimethylamino-8-exo-hydroxymethyl-7-endo-hydroxy-2-oxa-4-azabicyclo<3.3.0>oct-3-en-6-endo-yl 2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-allopyranosyl)-2-deoxy-β-D-allopyranoside 
• 165375-31-5 (1S,5S)-6-exo,7-endo-dibenzoyloxy-8-exo-benzyloxymethyl-3-dimethylamino-2-oxa-4-azabicyclo<3.3.0>octan-3-ene 
• 165375-30-4 (1S,5R)-6-exo,7-endo-dibenzoyloxy-8-exo-benzyloxymethyl-2-oxa-4-azabicyclo<3.3.0>octan-3-one 
• 103766-13-8 (1S,5R)-3-dimethylamino-6-exo-7-endo-dihydroxy-8-exo-hydroxymethyl-2-oxa-4-azabicyclo<3.3.0>oct-3-ene 
• 114621-71-5 3,4,6-tri-O-acetylallosamizoline 
• 138395-73-0 (3aS,4R,5R,6S,6aS)-6-(Acetoxymethyl)-2-oxohexahydro-2H-cyclopenta[d]oxazole-4,5-diyl diacetate 
• 124583-64-8 (1S,5R)-8-exo-benzyloxymethyl-3-dimethylamino-6-exo,7-endo-dihydroxy-2-oxa-4-azabicyclo<3.3.0>octan-3-ene 

Relevant academic research and scientific papers

IMPROVED AMINOHYDROXYLATION OF ALKENES

The invention relates to a process for the aminohydroxylation of alkenes using N-oxycarbamate reagents, e.g. N-acyloxycarbamate, N-alkyloxycarbonyloxycarbamate and N-aralkoxycarbonyloxycarbamate reagents. The invention particularly relates to an intermolecular aminohydroxylation reaction that can be carried out in the absence of added base. The invention also relates to novel N-oxycarbamate reagents that are stable crystalline materials. The process of the invention is useful in the synthesis of compounds having a vicinal amino alcohol moiety, such as biologically active compounds.

Alkyl 4-chlorobenzoyloxycarbamates as highly effective nitrogen source reagents for the base-free, intermolecular aminohydroxylation reaction

Ethyl-(7), benzyl-(8), tert-butyl-(9), and fluorenylmethyl-4- chlorobenzoyloxycarbamates (10) have been prepared as storable and easy-to-prepare nitrogen sources for use in the intermolecular Sharpless aminohydroxylation reaction and its asymmetric variant. These reagents were found to be effective under base-free reaction conditions. The scope and limitations of these methods have been explored using a variety of alkenes, among which, trans-cinnamates, in particular, proved to be good substrates.

Syntheses of the Fungicide/Insecticide Allosamidin and a Structural Isomer

A synthesis of the naturally occurring inhibitor of chitin metabolism, allosamidin 1, involves, as the key step, condensation between the allosamizoline derivative 39, prepared following oxyamination of the cyclopentene 19, and the disaccharide glycosylating agent 54 which was synthesised from 2-acetamido-2-deoxy-D-glucose.The structural isomer 59 of allosamidin is also reported.Brief biological test results obtained using isomers 1 and 59 are recorded.