904893-22-7

Upstream product

• 201290-06-4 3,4,6-tri-O-benzyl-1,2-dideoxy-D-xylo-hex-1-enitol 
• 16838-89-4 2,3,5-tri-O-benzyl-D-xylofuranose 
• 904893-23-8 (3S,4R,5R)-5-methanesulfonyloxy-3,4,6-tribenzyloxy-1-hexene 
• 913365-64-7 (2S,3S,4S)-2,3,5-Tris-benzyloxy-4-hydroxy-pentanal oxime 
• 96192-07-3 2,3,5-tri-O-benzyl-L-arabinofuranose 
• 913365-65-8 C₃₂H₄₂INO₄Si 
• 904893-24-9 (-)-(2R,3R,4R)-1,3,4-tris(benzyloxy)-5-oxopentan-2-yl methanesulfonate 

Downstream Products

• 904893-28-3 (2S,3S,4S,5S)-2-benzyloxymethyl-3,4-dibenzyloxy-5-(4-benzyloxyphenyl)-N-hydroxy-pyrrolidine 
• 904893-27-2 (2S,3S,4S,5S)-2-benzyloxymethyl-3,4-dibenzyloxy-5-(3-benzyloxy-4-methoxyphenyl)-N-hydroxy-pyrrolidine 
• 904893-25-0 (2S,3S,4S,5S)-2-benzyloxymethyl-3,4-dibenzyloxy-5-phenyl-N-hydroxy-pyrrolidine 
• 151265-55-3 (2S,3S,4S,5S)-2-hydroxymethyl-5-phenylpyrrolidine-3,4-diol 
• 905286-71-7 (2S,3S,4S,5S)-2-hydroxymethyl-3,4-dihydroxy-5-(3-hydroxy-4-methoxyphenyl)-pyrrolidine 
• 1231217-52-9 (2S,3S,4S,5S)-1-hydroxyl-3,4-bis-(benzyloxy)-2-((benzyloxy)methyl)-5-(3,3-dimethoxypropyl)pyrrolidine 
• 1245637-64-2 (2S,3S,4S,5R)-2-(benzyloxymethyl)-3,4-dibenzyloxy-5-(thiophen-2-yl)-N-hydroxy-pyrrolidine 
• 1245637-63-1 (2S,3S,4S,5S)-2-(benzyloxymethyl)-3,4-dibenzyloxy-5-(thiophen-2-yl)-N-hydroxy-pyrrolidine 
• 1245637-48-2 (2S,3S,4S,5S)-2-(benzyloxymethyl)-3,4-dibenzyloxy-5-(1H-indol-3-yl)-N-hydroxy-pyrrolidine 
• 1245637-57-3 (2S,3S,4S,5S)-2-(benzyloxymethyl)-3,4-dibenzyloxy-5-(5-fluoro-1H-indol-3-yl)-N-hydroxy-pyrrolidine 
• 1245637-59-5 (2S,3S,4S,5S)-3,4-dibenzyloxy-2-(benzyloxymethyl)-5-(1H-pyrrol-2-yl)-N-hydroxy-pyrrolidine 
• 1245637-60-8 (2S,3S,4S,5R)-3,4-dibenzyloxy-2-(benzyloxymethyl)-5-(1H-pyrrol-2-yl)-N-hydroxy-pyrrolidine 
• 1225027-14-4 2,4-di((2S,3S,4S,5S)-3,4-dibenzyloxy-5-(benzyloxymethyl)-1-hydroxypyrrolidin-2-yl)benzene-1,3,5-triol 
• 1245637-58-4 (2S,3S,4S,5S)-2-(benzyloxymethyl)-3,4-dibenzyloxy-5-(5-nitro-1H-indol-3-yl)-N-hydroxy-pyrrolidine 

Relevant academic research and scientific papers

Small structure tree alkali compound and its preparation method and application

The invention relates to a Broussonetia kazinoki alkaline compound. Structure of the compound is shown as a formula (1). The invention further provides a preparation method of the compound, a glycosidase inhibitor by using the compound or the compound prepared by the method as an active ingredient and application of the compound or the compound, prepared by the method, serving as an active ingredient in preparing drug. The Broussonetia kazinoki alkaline compound has high glycosidase inhibiting activity and potential medicinal value.

Polyhydroxylated pyrrolidine compound as well as preparation method and application thereof

The invention relates to the field of glycosidase inhibitors and particularly relates to a polyhydroxylated pyrrolidine compound as well as a preparation method and application thereof. The structure of the polyhydroxylated pyrrolidine compound is as shown in formula (I). The polyhydroxylated pyrrolidine compound has high glycosidase inhibition activity and has a potential medicinal value. The formula is as shown in description.

A practical synthesis of sugar-derived cyclic nitrones: Powerful synthons for the synthesis of iminosugars

Sugar-derived cyclic nitrones were synthesized from the corresponding aldoses through an efficient and practical procedure involving a seven-step reaction sequence in good to excellent overall yield (10-42%). This synthetic strategy, requiring only inexpe

A convenient approach toward the synthesis of enantiopure isomers of DMDP and ADMDP

A practical method for the synthesis of five-membered iminocyclitols, pyrrolidine alkaloids bearing multiple hydroxyl substituents, has been developed. All of the eight key intermediates, enantiopure tri-O-benzyl cyclic nitrones, are prepared from four cheap, readily available d-aldopentoses. The nucleophilic addition of cyclic nitrones with vinyl magnesium chloride and TMSCN shows high 2,3-trans stereoselectivity. To construct the 2,3-cis configurations, inversion of the C-2 nitrile group is achieved via an elimination-reduction sequence. Using this approach, five isomers of DMDP and six isomers of ADMDP are prepared efficiently. In the biological evaluation, iminocyclitol 27 is a new and potent inhibitor against β-hexosaminidase with an IC50 value of 0.2 μM.

Synthesis and biological evaluation of a 2-aryl polyhydroxylated pyrrolidine alkaloid-based library

Inspired by polyhydroxylated pyrrolidine alkaloid natural products, a 18-membered library of 2-aryl polyhydroxylated pyrrolidines has been efficiently prepared in two or three synthetic steps from the known chiral cyclic nitrones with high yield and purity and excellent stereoselectivity. The inhibitory activity of all these compounds against various glycosidase enzymes was evaluated. Interestingly, 15 and 19 show better inhibitory activities than radicamine A (20) and B (18) against α-glucosidases. The IC50 values of 15 and 19 are 1.1 and 0.5 μM, respectively. In this study, we also discovered the substituent(s) on the aryl ring could affect the inhibition potency and selectivity against glycosidases.

Radicamines A and B: Synthesis and revision of the absolute configuration

Starting from D-xylose, enantioselective syntheses of 1 and 2, the proposed structures for radicamines A and B, were accomplished. Both 1H and 13C NMR spectra of 1 and 2 were identical with those of the natural products, but the optical rotation measurements identified that 1 and 2 were actually the enantiomers of the natural radicamines A and B, respectively.

Total synthesis of (-)-radicamine B

The synthesis of a chiral cyclic nitrone with l-arabino configuration and its application in the total synthesis of radicamine B is reported. An agreement in the spectral data with natural radicamine B but specific rotation with an opposite sign warranted