151957-73-2

Upstream product

• 108-93-0 cyclohexanol 
• 151929-70-3 phenyl 2,6-anhydro-4-O-isobutyryl-3-C-methyl-1,2-dithio-L-mannopyranoside 
• 151929-69-0 methyl 2,6-anhydro-4-O-isobutyryl-3-C-methyl-2-thio-β-L-mannopyranoside 
• 151929-68-9 methyl 2,6-anhydro-3-C-methyl-2-thio-β-L-mannopyranoside 
• 137101-02-1 methyl 2,6-anhydro-4-O-benzyl-3-C-methyl-2-thio-β-L-mannopyranoside 
• 151957-70-9 cyclohexyl 2,6-anhydro-3-O-(2,6-anhydro-4-O-benzyl-2-thio-β-D-altropyranosyl)-4-O-benzyl-2-thio-β-D-mannopyranoside 
• 151929-66-7 cyclohexyl 2,6-anhydro-4-O-benzyl-2-thio-β-D-mannopyranoside 
• 151929-64-5 cyclohexyl 2,6-anhydro-4-O-benzyl-2-thio-β-D-altropyranoside 
• 151929-67-8 cyclohexyl 3-O-(3-O-acetyl-2,6-anhydro-4-O-benzyl-2-thio-β-D-altropyranosyl)-2,6-anhydro-4-O-benzyl-2-sulfinyl-β-D-mannopyranoside 
• 151957-71-0 cyclohexyl 2,6-anhydro-3-O-(2,6-anhydro-4-O-benzyl-2-thio-β-D-altropyranoside-3-ulosyl)-4-O-benzyl-2-thio-β-D-mannopyranoside 
• 151929-63-4 cyclohexyl 3-O-acetyl-2,6-anhydro-4-O-benzyl-2-thio-β-D-altropyranoside 
• 151957-69-6 cyclohexyl 2,6-anhydro-4-O-benzyl-2-sulfinyl-β-D-mannopyranoside 
• 151929-60-1 1,3-di-O-acetyl-2,6-anhydro-4-O-benzyl-2-thio-β-D-altropyranose 
• 151929-65-6 cyclohexyl 2,6-anhydro-4-O-benzyl-2-thio-β-D-altropyranoside-3-ulose 

Downstream Products

• 151929-71-4 cyclohexyl 2,6-dideoxy-3-O-<2,6-dideoxy-3-O-(2,6-dideoxy-3-O-(diethylisopropylsilyl)-4-O-isobutyryl-3-C-methyl-α-L-arabino-hexopyranosyl)-β-D-arabino-hexopyranosyl>-β-D-arabino-hexopyrnoside 

Relevant academic research and scientific papers

Application of highly stereocontrolled glycosidations employing 2,6-anhydro-2-thio sugars to the syntheses of erythromycin A and olivomycin A trisaccharide

The highly efficient syntheses of the erythromycin A (1) from its aglycon, (9S)-9-dihydroerythronolide A (4), and the C-D-E trisaccharide 3 of olivomycin A have been accomplished by the successful application of stereocontrolled glycosidations using 2,6-anhydro-2-thio sugars. The former synthesis includes the highly α-stereoselective glycosidation of the C5 desosaminated lactone 12 with phenyl 2,6-anhydro-4-O-benzyl-3-C-methyl-3-O-methyl-1,2-dithio-L-altropyranos ide (10), which was achieved by using NIS-TfOH. The latter synthesis involves both the highly β-stereoselective glycosidation of 1,3-di-O-acetyl-2,6-anhydro-4-O-benzyl-2-thio-β-D-altropyranose (23), which was realized by employing TMSOTf, and the highly α-stereoselective glycosidation of phenyl 2,6-anhydro-3-O-(diethylisopropylsilyl)-4-O-isobutyryl-3-C-methyl- 1,2-dithio-L-manno-pyranoside (24), which succeeded by utilizing NBS. Hydrogenolyses using Raney Ni as a catalyst and selective deprotections of the key glyco substances 17 and 22 led to the total syntheses of erythromycin A (1) and the C-D-E trisaccharide 3 of olivomycin A, respectively.

Total synthesis of the trisaccharide of olivomycin A

The total synthesis of the trisaccharide of olivomycin A, which is one of the aureolic acid antitumor antibiotics, has been achieved. Our approach involves highly stereocontrolled glycosidations using 2,6-anhydro-2-thio glycosyl donors. The 2,6-anhydro-2-