148404-74-4

Upstream product

• 98-88-4 benzoyl chloride 
• 127753-94-0 ethyl 1-thio-α-L-rhamnopyranoside 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-L-rhamnopyranose 
• 61198-83-2 1,2,3,4-tetra-O-benzoyl-α/β-L-rhamnopyranose 
• 75-08-1 ethanethiol 

Downstream Products

• 148404-64-2 3-benzyloxycarbonylaminopropyl 2,3,4-tri-O-benzoyl-α-L-rhamnopyranoside 
• 161007-95-0 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyltrichloroacetimidate 
• 250740-76-2 2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]ethyl 2-O-phenoxyacetyl-3-O-(2,3,4-tri-O-phenoxyacetyl-α-L-rhamnopyranosyl)-β-D-glucopyranose 
• 250740-74-0 2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]ethyl 2-O-acetyl-4,6-O-benzylidene-3-O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-β-D-glucopyranose 
• 250740-65-9 2-[3,4-bis(tert-butyldimethylsilyloxy)phenyl]ethyl 4,6-O-benzylidene-3-O-(α-L-rhamnopyranosyl)-β-D-glucopyranose 
• 648431-72-5 benzyl 2',3',4'-tri-O-benzoyl-α-L-rhamnopyranosyl-(1->3)-2-acetamido-4,6-di-O-acetyl-2-deoxy-α-D-glucopyranoside 
• 110825-24-6 benzyl α-L-rhamnopyranosyl-(1->3)-2-acetamido-2-deoxy-α-D-glucopyranoside 

Relevant academic research and scientific papers

Visible Light Enables Aerobic Iodine Catalyzed Glycosylation

A versatile protocol for light induced catalytic activation of thioglycosides using iodine as an inexpensive and readily available photocatalyst was developed. Oxygen serves as a green and cost-efficient terminal oxidant and irradiation is performed with a common household LED-bulb. The scope of this glycosylation protocol was investigated in the synthesis of O-glycosides with yields up to 95 %.

Synthesis of rhamnosylated diosgenyl glucosides as mimetics of cytostatic steroidal saponins from Ornithogalum saundersiae and Galtonia candicans

The synthesis of mimetic 3 of the steroid saponins 1 and 2 was investigated. As a substitute for the complex 22-homo-23-nor-steroid moieties A and B in 1 and 2 diosgenin C was introduced. The silyl protected thioorthoester 20 was successfully employed for glucosylation. After selective 2-O-deacetylation, the glucosylated diosgenyl acceptor 23 was rhamnosylated. The 4-O-p-methoxybenzoylated donor 12 gave only minor yields. By using the tri-O-benzoyl protected donor 15 the α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→3β) -diosgenin derivative 25 was obtained.

Syntheses of methyl (4,6-dideoxy-α-L-lyxo-hexopyranosyl)-(1→3)- and (4-deoxy-4-fluoro-α-L-rhamnopyranosyl)-(1→3)-2-acetamido-2-deoxy-α-D-glucopyranosides, analogs of the mycobacterial arabinogalactan linkage disaccharide

We have made thioglycoside donors for the 4,6-dideoxy-L-lyxo-hexopyranosyl ('4-deoxy-L-rhamnosyl') and 4-deoxy-4-fluoro-L-rhamnosyl monosaccharide residues. The preparation of the deoxyfluororhamnose was not straightforward, and revealed some unexpected behavior of the diethylaminosulfur trifluoride (DAST) reagent. The new glycosyl donors were used to synthesize two analogs of the mycobacterial arabinogalactan linkage disaccharide →4)-α-L-Rha-(1→3)-α-D-GlcNAc. These analogs are prototypes for a family of potential inhibitors of the enzymes involved in the early stages of cell-wall construction in mycobacteria. Copyright (C) 1999 Elsevier Science Ltd.