73991-13-6

Upstream product

• 73-34-7 L-rhamnose 
• 72657-01-3 1,2-O-(1-methoxyethylidene)-3,4-di-O-benzyl-β-L-rhamnopyranose 
• 1091625-31-8 3,4-di-O-benzyl-1,2-(allyloxyethylidene)-β-L-rhamnopyranose 
• 100-44-7 benzyl chloride 
• 127875-00-7 2-methoxyethyl 2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranoside 
• 141554-87-2 3,4-Di-O-Acetyl-β-L-rhamnose 1,2-(ethylorthoacetate) 
• 5158-64-5 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl bromide 
• 6014-42-2 L-rhamnose 
• 30021-94-4 1,2,3,4-O-tetraacetyl-α-L-rhamnopyranose 

Downstream Products

• 167013-82-3 2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl trichloroacetimidate 
• 73983-19-4 1,2-di-O-acetyl-3,4-di-O-benzyl-6-deoxy-α-L-mannopyranose 
• 73983-20-7 1,2-di-O-acetyl-3,4-di-O-benzyl-β-L-rhamnopyranose 

Relevant academic research and scientific papers

Dehydrative Glycosylation Enabled by a Comproportionation Reaction of 2-Aryl-1,3-dithiane 1-Oxide?

A new dehydrative glycosylation reaction has been established by capitalizing on the comproportionation reaction of 2-aryl-1,3-dithiane 1-oxides promoted by triflic anhydride (Tf2O). By wedding the high potency of thiophilic promoter system with the step efficiency of dehydrative glycosylation, this reagent underwent facile intermolecular oxothio acetalization with C1-hemiacetal donor to install a temporary leaving group, rendering a transient electrophilic center at the remote site to the anomeric position. The sulfenyl triflate tethered at the terminus concomitantly activated the sulfide intramolecularly to afford the oxocarbenium ion, thereby facilitating the title glycosylation. Aside from accommodating broad range functional groups and inactive hemiacetal substrates, the present activation protocol also proved expedient for 1,3-diol protection. Most importantly, this method further provided a fresh perspective for the application of sulfur chemistry to carbohydrate chemistry.

Synthesis of oligosaccharide fragments of the rhamnogalacturonan of Nerium indicum

Three trisaccharides, one pentasaccharide, and one heptasaccharide, namely α-D-GalA-(1→2)-α-L-Rha-(1→4)-β-D-GalA-OC 3H7 (1), α-L-Rha-(1→4)-α-D-GalA- (1→4)-β-D-GalA-OC3H7 (2), α-D-GalA- (1→4)-α-DGalA-(1→2)-α-L-Rh

Total synthesis of the phenolic glycolipid mycoside B and the glycosylated p-hydroxybenzoic acid methyl ester HBAD-I, virulence markers of mycobacterium tuberculosis

The phenolic glycolipid mycoside B, present in Mycobacterium bovis and hypervirulent strains of Mycobacterium tuberculosis, has been synthesized for the first time. Multiple methyl groups were introduced by the extensive use of catalytic asymmetric 1,4-addition reactions, asymmetric hydrogenation of a β-keto ester afforded the basis for the central 1,3-diol moiety, and introduction of the 2-O-methyl-α-L-rhamnoside unit was achieved by stereoselective glycosylation with p-iodophenol and subsequent Sonogashira coupling, providing a basis for the generation of analogues. In addition, the related monosaccharide HBAD-I, present in the same species, has been efficiently synthesized for the first time by selective methylation of the hydroxy group at C-2 of a rhamnoside. The phenolic glycolipid mycoside B and the related phenolic glycoside HBAD-I from Mycobacterium tuberculosis have been synthesized for the first time. A highly convergent strategy was used featuring catalytic asymmetric 1,4-additions of MeMgBr and Me2Zn and a late-stage Sonogashira coupling as the key steps. Copyright