167013-82-3

Upstream product

• 73983-18-3 2-O-acetyl-3,4-O-dibenzyl-α-L-rhamnopyranoside 
• 545-06-2 trichloroacetonitrile 
• 30021-94-4 1,2,3,4-O-tetraacetyl-α-L-rhamnopyranose 
• 6014-42-2 L-rhamnose 
• 5158-64-5 2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl bromide 
• 141554-87-2 3,4-Di-O-Acetyl-β-L-rhamnose 1,2-(ethylorthoacetate) 
• 73983-18-3 2-O-acetyl-3,4-di-O-benzyl-L-rhamnopyranose 
• 73983-19-4 1,2-di-O-acetyl-3,4-di-O-benzyl-6-deoxy-α-L-mannopyranose 
• 69980-52-5 2,3,4-tri-O-acetyl-L-rhamnopyranosyl bromide 

Downstream Products

• 176168-83-5 4-(1,3-Dioxolan-2-yl)-3-oxabutyl 2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranoside 
• 327162-28-7 methyl (2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->4)]-2-O-benzoyl-α-L-rhamnopyranoside 
• 327162-34-5 methyl (2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->2)-(3,4-di-O-benzyl-α-L-rhamnopyranosyl)-(1->3)-[2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->4)]-2-O-benzoyl-α-L-rhamnopyranoside 
• 1028832-92-9 methyl 2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl-(1->3)-4-O-benzyl-2-O-(naphthylmethyl)-β-L-rhamnopyranosyl-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 1239318-80-9 4-methoxyphenyl 2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl-(1->3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside 
• 1449576-20-8 p-iodophenyl 3,4-di-O-benzyl-α-L-rhamnopyranoside 
• 1449576-21-9 p-iodophenyl 3,4-di-O-benzyl-2-O-methyl-α-L-rhamnopyranoside 
• 1449576-22-0 4-[(17R,19R,24S,25R)-17,19-dihydroxy-25-methoxy-24-methylheptacos-1-ynyl]phenyl 3,4-di-O-benzyl-2-O-methyl-α-L-rhamnopyranoside 
• 1449576-19-5 p-iodophenyl 2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranoside 
• 176168-86-8 4-(1,3-Dioxolan-2-yl)-3-oxabutyl 3,4-di-O-benzyl-2-O-[3,4-di-O-benzyl-2-O-(2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranosyl]-α-L-rhamnopyranoside 
• 176168-85-7 4-(1,3-Dioxolan-2-yl)-3-oxabutyl 3,4-di-O-benzyl-2-O-(2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-α-L-rhamnopyranoside 

Relevant academic research and scientific papers

Total Syntheses of Aturanosides A and B

Total syntheses of aturanosides A and B, two antiangiogenic anthraquinone glycosides, have been achieved in an expeditious manner, highlighting anthraquinone synthesis, phenol glycosylation, α-d-glucosaminoside installation, and judicious use of protectin

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

Synthesis of the trisaccharide α-L-Rha-(1-2)-α-L-Rha-(1-2)-α-L-Rha with a dioxolane-type spacer-arm

The trisaccharide α-L-Rha-(1-2)-α-L-Rha-(1-2)-α-L-Rha with a dioxolane-type spacer was obtained by using the trichloroacetimidate method in all of the glycosidation steps. After deprotection, the trisaccharide was coupled to BSA or KLH by reductive aminat