84730-13-2

Upstream product

• 100-52-7 benzaldehyde 
• 16848-19-4 3-amino-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose 
• 2595-05-3 Diacetone D-glucose 
• 55951-90-1 1,2:5,6-di-O-isopropylidene-3-O-trifluoromethanesulfonyl-α-D-allofuranose 
• 93-97-0 benzoic acid anhydride 
• 84730-09-6 3-benzylidenimido-3-deoxy-1,2;5,6-di-O-isopropylidene-α-D-glucofuranose 
• 81645-62-7 3-Benzamido-3-desoxy-1,2;5,6-di-O-isopropyliden-α-D-glucofuranose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 100-46-9 benzylamine 

Relevant academic research and scientific papers

A method for preparing N-alkylated kanosamines from diacetone D-glucose

The aminoglycoside (AG) antibiotics have seen a resurgence in their clinical use given the increase in multi drug resistant bacterial infections. Campaigns to generate novel analogs show promise that structural modification can lead to compounds with improved pharmacological properties. The results described herein include a new method to synthesize mono-, di-, and mixed N-alkylated kanosamine sugars and their elaboration into novel glycosides that inhibit bacterial protein synthesis in vitro.

The direct and highly diastereoselective synthesis of 3,4-epoxy-2-piperidones. Application to the total synthesis and absolute configurational assignment of 3α,4α-epoxy-5β-pipermethystine

The substrate-controlled asymmetric total synthesis and absolute configurational assignment of biologically active 3α,4α-epoxy-5β-pipermethystine, a minor component in the aerial parts of kava, has been achieved by featuring, as a key step, the environmentally friendly and direct synthesis of 2,3-epoxyamides from allyl amines. By using the chiron approach, first a carbohydrate-derived dehydropiperidine was prepared and subjected to a stereoselective tandem C-H/CC oxidation reaction. In this attempt, the required α,α-trans-epoxy-2-piperidone skeleton of the kava metabolite precursor was not achieved, although the tandem oxidation was highly stereoselective. However, starting from non-carbohydrate 3-hydroxy-4,5-dehydropiperidine, and using the same tandem oxidation, the target intermediate was obtained in high yield and complete unprecedented anti-stereoselectivity. Since the proposed mechanistic course of this tandem oxidation implies the transient formation of an α,β-unsaturated amide followed by the subsequent epoxidation reaction, this second approach supports the previously established biotransformation proposal of (-)-pipermethystine to (-)-3α,4α-epoxy-5β-pipermethystine.

REDUCTION OF 1,2;5,6-DI-O-ISOPROPYLIDENE-α-D-GLUCOFURANOSE DERIVATIVES WITH LITHIUM ALUMINIUM HYDRIDE; A FACILE SYNTHETIC METHOD FOR 3,6-IMINO DERIVATIVES

Treatment of 3-acylamido- or alkylimino-3-deoxy-1,2;5,6-di-O-isopropylidene-α-D-glucofuranose with lithium aluminium hydride in boiling 1,4-dioxane afforded unusual products, namely, 3,6-N-alkylimino-3,6-dideoxy-1,2-O-isopropylidene-α-D-glucofuranose or 6