284031-48-7

Upstream product

• 58475-16-4 [(2R)-2-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d] [1,3]dioxol-5-yl]-2-hydroxy-ethyl]4-methylbenzenesulfonate 
• 174626-23-4 (6S)-1-aza-3,4-didehydro-8-oxabicyclo[4.3.0]nonan-9-one 
• 1353648-30-2 (2S,4R,5S)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4,5-dihydroxypiperidine-1-carboxylate 
• 104048-51-3 (R)-1-((S)-3-Benzyloxymethyl-4,5-dihydro-isoxazol-5-yl)-ethane-1,2-diol 
• 1353648-31-3 (2S,4S,5R)-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-4,5-dihydroxypiperidine-1-carboxylate 
• 284031-17-0 (R)-2-azido-1-((3aR,5S,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl)ethan-1-ol 
• 4613-62-1 3-deoxy-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside 
• 4005-46-3 3-deoxy-1,2-O-isopropylidene-D-glucose 

Relevant academic research and scientific papers

Chemoselective room temperature E1cB N-N cleavage of oxazolidinone hydrazides from enantioselective aldehyde α-hydrazination: Synthesis of (+)-1,4-dideoxyallonojirimycin

Room temperature E1cB N-N cleavage of oxazolidinone hydrazides via N-alkylation with diethyl bromomalonate and potassium or caesium carbonate as base in acetonitrile is presented. The new method has a much improved chemoselectivity, which is illustrated by a concise total synthesis of the piperidine iminosugar (+)-1,4-dideoxyallonojirimycin.

Chemo-enzymatic synthesis of the azasugars 1,4-dideoxyallonojirimycin and 1,4-dideoxymannojirimycin

The enzymatic resolution of the N-phenylacetyl derivative of racemic homoserine lactone with penicillin G acylase immobilized on Eupergit C gave (R)-(+)-α-amino-γ-butyrolactone and (S)-(-)-α-N- phenylacetamido-γ-butyrolactone in high enantiomeric purity (ee >99%) and 46-47% yields for each enantiomer. The enantiomers were converted into azasugars 1,4-dideoxyallonojirimycin and 1,4-dideoxymannojirimycin using Wittig olefination, catalytic ring-closing metathesis (RCM), and stereoselective dihydroxylation with OsO4 in 29% overall yield over 11 high yielding steps. Enzyme inhibition studies showed that 1,4-dideoxyallonojirimycin is a better β-glucosidase inhibitor (IC50 32.4 μM toward β-glucosidase from almonds) and a better β-galactosidase inhibitor (IC50 5.9 mM for β-galactosidase from Aspergillus oryzae) than 1,4-dideoxymannojirimycin (IC50 2.86 mM and 12.5 mM for β-glucosidase and β-galactosidase, respectively).

A facile synthesis of a new trihydroxy piperidine derivative and (+)-proto-quercitol from D-(-)-quinic acid

We described herein the new synthesis of a trihydroxy piperidine derivative (1,4,5-trideoxy-1,5-imino-D-ribo-hexitol) and (+)-proto-quercitol from D-(-)-quinic acid, both are considered as inhibitors for glycosidases.

First stereocontrolled reduction of isoxazoline by hydrogenolysis: A new route to iminosugars via cyclic sulfates

The synthesis of four new trihydroxylated piperidines, considered as analogues of 1-deoxynojirimycin (DNJ) and 1-deoxymannojirimycin (DMJ), was achieved using cyclic sulfate substituted isoxazoline derivatives. The key step is the one-pot reduction of an

Syntheses of sugar-related trihydroxyazepanes from simple carbohydrates and their activities as reversible glycosidase inhibitors

Five diastereomeric trideoxy-1,6-iminohexitols were synthesised, and their inhibitory activities were determined against selected glycosidases. For comparison, 1,4,5-trideoxy-1,5-imino-D-lyxo-hexitol, the 4-deoxy derivative of 1-deoxymannojirimicin, was prepared by enzymatic isomerisation of 6-azido-3,6-dideoxy-D-ribo-hexose into the corresponding 2-ulose and subsequent hydrogenation accompanied by intramolecular reductive amination. (C) 2000 Elsevier Science Ltd.