138505-43-8

Basic information

• Product Name: (9S)-3-O-(2,6-anhydro-4-O-benzyl-3-C-methyl-3-O-methyl-2-thio-α-L-altropyranosyl)-9-dihydro-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)erythronolide A N-Oxide
• Synonyms: (9S)-3-O-(2,6-anhydro-4-O-benzyl-3-C-methyl-3-O-methyl-2-thio-α-L-altropyranosyl)-9-dihydro-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)erythronolide A N-Oxide
• CAS NO: 138505-43-8
• Molecular Weight: 930.165
• Mol File: 138505-43-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (9S)-3-O-(2,6-anhydro-4-O-benzyl-3-C-methyl-3-O-methyl-2-thio-α-L-altropyranosyl)-9-dihydro-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)erythronolide A N-Oxide(CAS DataBase Reference)
• NIST Chemistry Reference: (9S)-3-O-(2,6-anhydro-4-O-benzyl-3-C-methyl-3-O-methyl-2-thio-α-L-altropyranosyl)-9-dihydro-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)erythronolide A N-Oxide(138505-43-8)
• EPA Substance Registry System: (9S)-3-O-(2,6-anhydro-4-O-benzyl-3-C-methyl-3-O-methyl-2-thio-α-L-altropyranosyl)-9-dihydro-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)erythronolide A N-Oxide(138505-43-8)

Safety Data

• Hazardous Substances Data: 138505-43-8(Hazardous Substances Data)

Upstream product

• 15562-19-3 9S-Dihydroerythronolide A aglycon 
• 138505-34-7 (9S)-9-dihydro-9,11-O-isopropylideneerythronolide A 
• 138505-32-5 (9S)-9-dihydro-3,5-O-(p-methoxybenzylidene)erythronolide A 
• 138505-33-6 (9S)-9-dihydro-9,11-O-isopropylidene-3,5-O-(p-methoxybenzylidene)erythronolide 
• 138505-35-8 (9S)-9-dihydro-9,11-O-isopropylidene-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)erythronolide 
• 138505-36-9 (9S)-9-dihydro-9,11-O-isopropylidene-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)erythronolide A N-oxide 
• 137101-04-3 methyl 2,6-anhydro-4-O-benzyl-3-C-methyl-3-O-methyl-2-thio-α-L-altropyranoside 
• 138505-37-0 (1R,3S,4R,7S,8S)-7-Benzyloxy-8-methoxy-8-methyl-3-phenylsulfanyl-2-oxa-5-thia-bicyclo[2.2.2]octane 
• 138603-63-1 1-(2-pyrimidinethio) 3,4,6-trideoxy-2-O-methoxycarbonyl-3-(dimethylamino)-D-xylo-hexopyranoside 
• 168072-11-5 phenyl 2,6-anhydro-4-O-benzyl-3-C-methyl-3-O-methyl-1,2-dithio-β-L-altro-pyranoside 
• 138505-42-7 (9S)-3-O-(2,6-anhydro-4-O-benzyl-3-C-methyl-3-O-methyl-2-thio-α-L-altropyranosyl)-9-dihydro-9,11-O-isopropylidene-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)erythronolide A N-Oxide 

Downstream Products

• 114-07-8 erythromycin 
• 992-65-4 erythromycin A N-oxide 

Relevant articles and documents

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.