152434-63-4

Upstream product

• 98-88-4 benzoyl chloride 
• 181049-42-3 3-O-benzyl-5-deoxy-1,2-O-isopropylidene-5-nitromethyl-α-D-glucofuranose 
• 86495-59-2 (E)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-6-nitro-α-D-xylo-hex-5-eno-1,4-furanose 
• 5040-08-4 1,2-O-isopropylidene-α-D-xylo-5-hexulofuranurono-6,3-lactone 
• 152434-60-1 (3aR,3bS,6S,6aS,7aR)-6-Hydroxy-2,2-dimethyl-6-nitromethyl-tetrahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxol-5-one 
• 161068-30-0 (3aR,3bS,6S,6aS,7aR)-6-(1-Ethoxy-ethoxy)-2,2-dimethyl-6-nitromethyl-tetrahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxol-5-one 
• 152434-61-2 (3aR,3bS,6S,6aS,7aR)-6-(2-Ethoxy-ethoxy)-2,2-dimethyl-6-nitromethyl-tetrahydro-furo[2',3':4,5]furo[2,3-d][1,3]dioxol-5-one 
• 181049-36-5 (S)-2-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-3-nitro-propionaldehyde 

Downstream Products

• 86117-82-0 (1R)-(+)-(1,3,5/2,4)-2,3,4,5-tetrahydroxycyclohexane-1-methanol 
• 32780-32-8 validamine 
• 68108-50-9 (1S)-(+)-(1,2,4/3,5)-1-acetamido-2,3,4-triacetoxy-5-acetoxymethylcyclohexane 
• 94943-08-5 (1S)-(+)-(1,3/2,4,5)-2,3,4,5-tetrahydroxycyclohexanemethanol 

Relevant academic research and scientific papers

Stereoselective conversion of D-glucuronolactone into pseudosugar: Synthesis of pseudo-α-D-glucopyranose, pseudo-β-D-glucopyranose, and validamine

Two optically active pseudo-sugars, pseudo-α-D-glucopyranose (12) and pseudo-β-D-glucopyranose (13), were synthesized from D-glucuronolactone in favorable overall yields by using a stereoselective nitromethane addition reaction and a reductive elimination of an ethoxyethoxyl moiety with NaBH4 as key steps. Furthermore, a biologically active pseudo-aminosguar, validamine (18) was efficiently synthesized via a substitution reaction for an acetoxyl group at the β-position of nitro group in a nitrocyclitol derivative (14) which was prepared from a synthetic intermediate (9) of pseudo-d-glucopyranoses (12,13).

Syntheses of pseudo-α-D-glucopyranose, pseudo-β-D-glucopyranose, and validamine from D-glucuronolactone

Using a stereoselective nitromethane addition and a reductive elimination of an ethoxyethoxyl moiety with NaBH4 as key steps, two optically active pseudo-sugars, pseudo-α-D-glucopyranose and pseudo-β-D-glucopyranose, were synthesized from D-glucuronolactone in favorable overall yield. Furthermore, a biologically active pseudo-aminosugar, validamine, was synthesized via a substitution reaction for an acetoxyl group at the β-position of the nitro group in the nitrocyclitol derivative which was prepared from a synthetic intermediate of pseudo-D-glucopyranose.

Formaldehyde dimethylhydrazone: A new neutral reagent for nucleophilic hydroformylation and hydrocyanation

The readily available title compound smoothly adds to nitroolefins without any need of base or catalysis, giving β-nitrodimethylhydrazones 3 in high yields. Michael adducts 3 have been successfully transformed into β-nitroaldehydes by ozonolysis and in β-nitronitriles in excellent yields by treatment with MMPP. Therefore, formaldehyde dimethylhydrazone behaves as a new neutral formyl anion and cyanide equivalent, introducing a functionalized carbon unit β to the nitro group of a nitroolefin. Good yields and high stereoselectivities were obtained in the addition of 1 to a nitroolefin group within sugar derivatives, and no epimerization was observed in the cleavage of the dimethylhydrazone group.