270923-05-2

Upstream product

• 33647-85-7 isolevoglucosenone 
• 113019-43-5 2,3,4,6-tetra-O-benzyl-1-formyl-D-glucopyranose 
• 270923-04-1 1,6-anhydro-3-C-[(1S)-2,6-anhydro-3,4,5,7-tetra-O-benzyl-D-glycero-D-gulo-heptitol-1-C-yl]-2,3-dideoxy-β-D-glycero-hex-2-en-4-ulopyranose 

Downstream Products

• 270923-06-3 1,6:2,3-dianhydro-3-C-[(1S)-2,6-anhydro-3,4,5,7-tetra-O-benzyl-D-glycero-D-gulo-heptitol-1-C-yl]-β-D-gulo-pyranose 
• 270923-11-0 1,6:2,3-dianhydro-3-C-[(1S)-2,6-anhydro-3,4,5,7-tetra-O-benzyl-D-glycero-D-gulo-heptitol-1-C-yl]-β-D-gulo-pyranose-1',4-acetonide 
• 358369-20-7 1,6:2,3-dianhydro-3-C-[(1R)-2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-1-fluoro-D-glycero-D-gulo-heptitol-1-C-yl]-β-D-gulo-pyranose 
• 358369-16-1 1,6:2,3-dianhydro-3-C-[(1R)-2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-1-fluoro-D-glycero-D-gulo-heptitol-1-C-yl]-β-D-ribo-hex-4-ulopyranose 

Relevant academic research and scientific papers

Synthesis and solution conformational analysis of 2,3-anhydro-3-C-[(1R)-2, 6-anhydro-1-deoxy-1-fluoro-D-glycero-D-guloheptitol-1-C-yl]-β -D-gulo-furanose: First example of a monofluoromethylene-linked C-disaccharide

Condensation of 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosylcarbaldehyde with isolevoglucosenone induced by Et2AlI, followed by epoxidation, gave an aldol that was fluorinated into a monofluoromethylene C-glucopyranoside that was converted into the title C-disaccharide 1. Its conformational behavior in water has been studied by using a combination of NMR spectroscopy (J and NOE data) and molecular mechanics calculations.

Convergent syntheses of C(1→3)-linked disaccharides starting from isolevoglucosenone

Nucleophilic addition (Nu-M+) to isolevoglucosenone 1 generates enolates stereospecifically (exo face addition) that can be reacted with sugar-derived aldehydes to give C(1→3)-linked disaccharide precursors with high diastereoselectivity. Limitations of the method arising from unfavorable aldolate stability can be overcome by using Et2AlI as the nucleophile. This leads to products of Baylis-Hillmann condensations. One example is presented and has led to the preparation of 2,3-anhydro-3-C-[(1S)-2,6-anhydro-D-glycero-D-gulo-heptitol-1-C-yl]-β-D-gulo-pyranose 5. Copyright (C) 2000 Elsevier Science Ltd.