139195-45-2

Upstream product

• 89160-12-3 C₆₃H₆₄O₁₀ 
• 133697-34-4 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol 
• 89064-71-1 β-C-(hydroxymethyl)-2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside 
• 252851-40-4 methyl 2,3,4-tri-O-benzyl-6-deoxy-6-mercapto-α-D-glucopyranoside 
• 441044-62-8 methyl 6-S-acetyl-2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranoside 
• 246864-26-6 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-1-iodo-D-glycero-D-gulo-heptitol 
• 441044-63-9 methyl 2,3,4-tri-O-benzyl-6-S-(2',6'-anhydro-3',4',5',7'-tetra-O-benzyl-1'-deoxy-D-glycero-D-gulo-heptitol-1-yl)-6-thio-α-D-glucopyranoside 
• 85716-43-4 methyl 6-deoxy-6-iodo-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 252851-42-6 methyl S,S-dioxo-2,3,4-tri-O-benzyl-6-S-(2',6'-anhydro-3',4',5',7'-tetra-O-benzyl-1'-deoxy-D-glycero-D-gulo-heptitol-1-yl)-6-thio-α-D-glucopyranoside 

Downstream Products

• 139195-46-3 C₆₃H₆₇⁽²⁾HO₁₁ 
• 139242-12-9 methyl 8,12-anhydro-2,3,4,9,10,11,13-hepta-O-benzyl-6,7-dideoxy-α-D-glycero-D-gulo-D-gluco-tridecopyranoside 
• 139195-49-6 C₃₆H₃₉⁽²⁾HO₆ 
• 139195-47-4 C₆₃H₆₇⁽²⁾HO₁₀ 

Relevant academic research and scientific papers

A Ramberg-Baecklund approach to the synthesis of C-glycosides, C-linked disaccharides, and C-glycosyl amino acids

Synthetic applications of exo-glycals, derived from S-glycoside dioxides using the Meyers variant of the Ramberg-Baecklund rearrangement, are described. These include a formal synthesis of a β-glycosidase inhibitor 12 and an efficient route to spirocyclic glucose derivatives 17 and 18. The synthesis of C-linked disaccharides 24, 31, and 38 and the C-glycosyl amino acid 49 using the Ramberg-Baecklund rearrangement is also reported. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

Synthesis of α- and β-D-(1→6)-C-Disaccharides by Wittig Olefination of Formyl C-Glycosides with Glycopyranose 6-Phosphoranes

The synthesis of (1→6)-C-disaccharides by Wittig condensation of formyl C-glycofuranosides and pyranosides with galacto- and glucopyranose 6-phosphoranes is described herein. The method involves the coupling of the sugar aldehydes with the ylides and the reduction of the double bond of the resulting sugar alkenes, in most of the cases by catalytic hydrogenation. The reduction with nickel boride or diimide is employed in some special cases. O-Benzyl protective groups are removed by catalytic hydrogenation either in the course of the reduction of the double bond or in a subsequent step, while O-isopropylidene groups are cleaved by treatment with Amberlite IR-120. In this way, eight free β-D-(1→6)-C-disaccharides have been prepared in 26-61% overall yield starting from β-linked formyl C-glycosides. These include C-linked analogues of the biologically active disaccharides allolactose (Galβ1,6Glc), gentiobiose (Glcβ1,6Glc), and N-acetylamino disaccharides (GalNHAcβ1,6Gal and GalNHAcβ1,6Glc). Moreover, the synthesis of two α-D-(1→6)-C-disaccharides is described from formyl C-furanosides. The limiting condition of the synthesis of these stereoisomers is the configurational instability of the α-linked formyl C-glycosides under the basic conditions of the Wittig olefination.

Preferred Conformation of C-Glycosides. 7. Preferred Conformation of Carbon Analogues of Isomaltose and Gentiobiose

The preferred solution conformation of the 1,6-linked C-disaccharides 3 and 4, carbon analogues of methyl isomaltoside and methyl gentiobioside, was shown to be 3-A and 4-A, respectively, by 1H NMR spectroscopy.