32785-99-2

Upstream product

• 16749-46-5 6-deoxy-1,2-O-isopropylidene-β-L-idofuranose 
• 87357-54-8 6-deoxy-1,2:3,5-di-O-isopropylidene-α-D-xylo-hex-5-enofuranose 
• 38838-11-8 6-bromo-6-deoxy-1,2:3,5-di-O-isopropylidene-α-D-glucofuranose 
• 81562-09-6 6-hydroxy-1,2:3,5-di-O-isopropylidene-α-D-glucofuranoside 
• 7595-86-0 O³,O⁵-((Ξ)-benzylidene)-O¹,O²-isopropylidene-O⁶-(toluene-4-sulfonyl)-α-D-glucofuranose 
• 24877-08-5 1,2:3,5-di-O-isopropylidene-6-deoxy-6-iodo-α-D-glucofuranose 
• 17668-66-5 6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose 
• 34322-91-3 1,2:3,5-bis-O-(1-methylethylidene)-6-(p-tolylsulfonyl)-α-D-glucofuranose 
• 26275-20-7 6-deoxy-1,2-O-isopropylidene-6-(4'-methylbenzene)sulfonyloxy-D-glucofuranose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 18549-40-1 1,2-O-isopropylidene-α-D-glucofuranose 
• 194875-04-2 O³,O⁵-((Ξ)-benzylidene)-O¹,O²-isopropylidene-6-iodo-6-deoxy-α-D-glucofuranose 
• 19189-71-0 O³,O⁵-((Ξ)-benzylidene)-O¹,O²-isopropylidene-α-D-xylo-6-deoxy-hex-5-enofuranose 
• 258521-65-2 6-tosyl-1,2:3,5-di-O-isopropylidene-β-L-idofuranoside 

Downstream Products

• 16749-46-5 6-deoxy-1,2-O-isopropylidene-β-L-idofuranose 
• 17668-66-5 6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose 

Relevant academic research and scientific papers

C1-symmetric diphosphite ligands derived from carbohydrates: Influence of structural modifications on the rhodium-catalyzed asymmetric hydroformylation of styrene

New 3,5-diphosphite-substituted xylofuranoside (1b, 25a,b, and 26a,b) and glucofuranoside (3a, 7a, 8a,b) ligands with C1 symmetry have been prepared and used in the Rh-catalyzed asymmetric hydroformylation of styrene. The main structural features of these ligands are a) the presence of a 6-O-isopropyl group in ligands with a gluco configuration, b) the absence of 1,2-O-isopropylidene, a common group in many ligands with a furanoside skeleton, c) the presence of an alkyl chain bound to the 2-OH, and d) modification of the diol in the phosphite moiety. Modification of the carbohydrate backbone and diphosphite bridge affects the activity and selectivity of the reaction. Catalytic systems with ligands 1b and 8b were not active at 40 °C, although the formation of the expected hydride species [RhH(CO)2(1b)] was demonstrated by NMR spectroscopy. The highest enantioselectivity (83%) was obtained with the catalytic system Rh/8a. The complex [RhH(CO)2(8a)] was characterized by NMR spectroscopy using high-pressure techniques and was shown to exist in solution as two isomers in equilibrium; the two isomers adopt an equatorial-equatorial (eq-eq) configuration. Wiley-VCH Verlag GmbH & Co. KGaA, 2009.

Biologically potent L-hexoses and 6-deoxy-L-hexoses: Their syntheses and applications

This account describes our recent work in the development of new methodologies to prepare rare and biologically potent L-hexoses and 6-deoxy-L-hexoses, from cheapest D-glucose, via L-hexofuranoses and 1,6-anhydro-β-L-hexopyranoses as key building blocks. Their applications in the syntheses of heparin oligosaccharides, the carbohydrate moiety of bleomycin A2, and L-acovenose are also summarized here.

Synthesis of 6-deoxy-L-idose and L-acovenose from 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

A practical route toward the synthesis of 6-deoxy-L-idose and L-acovenose from 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose is described. Key steps include the stereoselective hydrogenation of 6-deoxy-1,2:3,5-di-O-isopropylidene-α-D-xylo-hex-5-enofuranose, regioselective protection of 6-deoxy-1,2-O-isopropylidene-β-L-idofuranose at O-5, and epimerisation of 6-deoxy-5-O-tert-butyldimethylsilyl-1,2-O-isopropylidene-β-L-idofuranose at C-3.

Novel synthesis of 1,2:3,5-di-O-isopropylidene-β-L-idofuranoside and its derivatives at C6

An efficient synthesis of 1,2:3,5-di-O-isopropylidene-β-L-idofuranoside and its derivatives at C6 from diacetone α-D-glucose employing the stereoselective hydroboration and hydrogenation as key steps is described here.