153693-37-9

Upstream product

• 108-24-7 acetic anhydride 
• 131087-35-9 phenyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside 
• 1214-98-8 phenyl 1-thio-α-L-rhamnopyranose 

Downstream Products

• 153693-41-5 2-((tert-butyldiphenylsilyloxy)methyl)-5-<(4-O-acetyl-6-deoxy-3-O-methyl-2-O-pivaloyl-α-L-mannopyranosyl)oxy>-3,4-dimethoxy-6-iodotoluene 
• 153693-42-6 4-<(-4-O-acetyl-6-deoxy-3-O-methyl-2-O-pivaloyl-α-L-mannopyranosyl)oxy>-2,3-dimethoxy-5-iodo-6-methylbenzoic acid 
• 153693-30-2 bis(ethyloxy)phosphinoyl-4-<(6-deoxy-3-O-methyl-α-L-mannopyranosyl)oxy>-5-iodo-2,3-dimethoxy-6-methylbenzoate 
• 153693-57-3 2,2-Dimethyl-propionic acid (2S,3R,4R,5S,6S)-5-acetoxy-2-(4-hydroxymethyl-2-iodo-5,6-dimethoxy-3-methyl-phenoxy)-4-methoxy-6-methyl-tetrahydro-pyran-3-yl ester 
• 153693-39-1 4-O-acetyl-6-deoxy-3-O-methyl-2-O-pivaloyl-1-phenylsulfinyl-α-L-mannopyranose 
• 153693-58-4 4-(6-Deoxy-3-O-methyl-α-L-mannopyranosyloxy)-3-iodo-5,6-dimethoxy-2-methylbenzoic acid 
• 153693-38-0 phenyl 4-O-acetyl-6-deoxy-3-O-methyl-2-O-pivaloyl-1-thio-α-L-mannopyranoside 
• 129834-73-7 methyl 4,6-dideoxy-4-<<<2,6-dideoxy-4-S-<4-<<3-O-methyl-α-L-rhamnopyranosyl>oxy>-5-iodo-2,3-dimethoxy-6-methylbenzoyl>-4-thio-β-D-ribo-hexopyranosyl>oxy>amino>-2-O-<2,4-dideoxy-4-(ethylamino)-3-O-methyl-α-L-threo-pentopyranosyl>-β-D-glucopyranoside 
• 146399-77-1 phenyl 4-O-benzyl-2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside 
• 172276-94-7 phenyl 4-O-acetyl-1-thio-α-L-rhamnopyranoside 

Relevant academic research and scientific papers

Slow glycosylation: Activation of trichloroacetimidates under mild conditions using lithium salts and the role of counterions

Glycosylations were carried out with the two glycosyl donors 4-O-acetyl-2,3-O-isopropylidene-1-O-trichloroacetimidoyl-α-L-rhamnopyranose and 2,3,4-tri-O-benzyl-1-O-trichloro-acetimidoyl-α-L-rhamnopyranose in combination with the two alcohols 1-adamantanol and L-menthol as model glycosyl acceptors. As catalysts, the five lithium salts LiNTf2, LiI, LiClO4, LiPF6 and LiOTf were investigated. We demonstrated that both lithium and the respective counterions are playing a role in the activation of trichloroacetimidate glycosyl donors at rt. Under these very mild conditions, the glycosylations are slow and completed in two to eight days. Depending on the counterion, the rate and yield of the reaction differs; however, the selectivity of all investigated lithium salts is deficient.

Synthesis of all eight L-glycopyranosyl donors using C-H activation

The synthesis of all eight rare, but biologically important L-hexoses as the according thioglycosyl donors was achieved through a procedure involving the C-H activation of their corresponding 6-deoxy-L-hexoses. The key steps of the procedure were the silylation of the OH group at C4 followed by an intramolecular C-H activation of the methyl group in g-position; both steps were catalyzed by iridium. The following Fleming-Tamao oxidation and acetylation gave the suitably protected L-hexoses. This is the first general method for the preparation of all eight L-hexoses as their thioglycosyl donors ready for glycosylation and the first example of an iridium-catalyzed C(sp3)-H activation on sulfide-containing compounds.

Concise synthesis of the calicheamicin oligosaccharide using the sulfoxide glycosylation method

A short synthesis of the calicheamicin oligosaccharide is reported. All the glycosidic linkages have been constructed using the sulfoxide glycosylation reaction, demonstrating the efficacy of the method. A general method to introduce N-O glycosidic linkag