107690-56-2

Upstream product

• 115996-13-9 1-((3aR,6aR)-2-Hydroxy-hexahydro-furo[3,2-b]pyrrol-4-yl)-ethanone 
• 107690-64-2 methyl 3,6-acetylepimino-2,3,5,6-tetradeoxy-β-D-threo-hexofuranoside 
• 13964-23-3 3-azido-3-deoxy-1,2:5,6-di-(O-isopropylidene)-α-D-glucofuranose 
• 107690-59-5 3-azido-3,5-dideoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose mesylate 
• 107690-62-0 methyl 3,6-acetylepimino-3,5,6-trideoxy-β-D-xylo-hexofuranoside 
• 20402-40-8 3,6-acetylepimino-3,6-dideoxy-1,2-O-isopropylidene-α-D-glucofuranose 
• 22169-72-8 3-azido-3-deoxy-6-O-toluene-p-sulphonyl-1,2-O-isopropylidene-α-D-glucofuranose 
• 84730-20-1 3,6-epimino-3,6-dideoxy-1,2-O-isopropylidene-α-D-glucofuranose 
• 115996-14-0 3-amino-3-deoxy-6-O-toluene-p-sulphonyl-1,2-O-isopropylidene-α-D-glucofuranose 
• 115996-16-2 methyl 3,6-acetylepimino-3,6-dideoxy-2,5-dithiocarbamoyl-(α,β)-D-glucofuranoside 
• 107690-63-1 methyl 3,6-acetylepimino-3,5,6-trideoxy-2-S-carbamoyl-(α,β)-D-xylo-hexofuranoside 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 107690-63-1 Dithiocarbonic acid O-((2R,3R,3aS,6aR)-4-acetyl-2-methoxy-hexahydro-furo[3,2-b]pyrrol-3-yl) ester S-methyl ester 
• 96625-41-1 3-azido-3-deoxy-1,2-O-isopropylidene-5,6-di-O-mesyl-α-D-glucofuranose 

Relevant academic research and scientific papers

2,5-Dihydropyrrole derivatives as enantiomerically enriched building blocks: Synthesis of the Geissman-Waiss lactone and polyhydroxylated pyrrolidines

Starting from enantiomerically pure 2,5-dihydropyrroles substituted at 2-position, efficient stereoselective syntheses of the (+)-Geissman-Waiss lactone and of (+)-1,4,5-trideoxy-1,4-imino-D-ribo-hexitol hydrochloride have been achieved. This work illustrates the high potential of 2,5-dihydropyrroles for the obtention of polyhydroxylated nitrogen heterocycles. Copyright (C) Elsevier Science Ltd.

Synthesis of N-Acetyl Derivatives of (1R,5R)-6-Aza-2-oxabicyclooctan-3-one and (1S,5R,8R)-8-O-Benzyl-6-aza-2-oxabicyclooctan-3-one from D-Glucose

N-Acetyl derivatives of (1R,5R)-6-aza-2-oxa-bicyclooctan-3-one (5) and (1S,5R,8R)-8-O-benzyl-6-aza-2-oxa-bicyclooctan-3-one (6), suitable chiral intermediates for (+)-retronecine (1) and (+)-crotanecine (2), have been synthesised from D-gluc

Synthesis of N-Acetyl-(1R,5R)-6-aza-2-oxabicyclooctan-3-one

A fifteen-step synthesis of N-acetyl-(1R,5R)-6-aza-2-oxabicyclooctan-3-one (Geissman-Waiss lactone), an established chiral precursor for (+)-retronecine, is described starting from D-glucose.