131675-54-2

Upstream product

• 1214-98-8 phenyl 1-thio-α-L-rhamnopyranose 
• 74-88-4 methyl iodide 
• 73-34-7 L-rhamnose 
• 108740-74-5 phenyl 2,3,4-tri-O-acetyl-1-thio-α-L-rhamnopyranoside 
• 30021-94-4 1,2,3,4-O-tetraacetyl-α-L-rhamnopyranose 
• 108-98-5 thiophenol 

Downstream Products

• 131675-55-3 phenyl 2,4-di-O-acetyl-3-O-methyl-1-thio-α-L-rhamnopyranoside 
• 130851-56-8 methyl 4-<<3-O-methyl-α-L-rhamnopyranosyl>oxy>-5-iodo-2,3-dimethoxy-6-methylbenzoate 
• 131675-57-5 methyl 4-<<2,4-di-O-acetyl-3-O-methyl-α-L-rhamnopyranosyl>oxy>-5-iodo-2,3-dimethoxy-6-methylbenzoate 
• 131675-59-7 4-<<3-O-methyl-2,4-bis-O-(triethylsilyl)-α-L-rhamnopyranosyl>oxy>-5-iodo-2,3-dimethoxy-6-methylbenzyl alcohol 
• 129834-75-9 4-<(6-deoxy-3-O-methyl-2,4-O,O-bis(triethylsilyl)-α-L-mannopyranosyl)oxy>-5-iodo-2,3-dimethoxy-6-methylbenzoic acid chloride 
• 129834-74-8 4-<<3-O-methyl-2,4-bis-O-(triethylsilyl)-α-L-rhamnopyranosyl>oxy>-5-iodo-2,3-dimethoxy-6-methylbenzoic acid 
• 131675-58-6 methyl 4-<<3-O-methyl-2,4-bis-O-(triethylsilyl)-α-L-rhamnopyranosyl>oxy>-5-iodo-2,3-dimethoxy-6-methylbenzoate 
• 150650-46-7 4-<<3-O-methyl-2,4-bis-O-(triethylsilyl)-α-L-rhamnopyranosyl>oxy>-5-iodo-2,3-dimethoxy-6-methylbenzaldehyde 
• 55836-48-1 2,4-di-O-acetyl-3-O-methyl-β-L-rhamnopyranose 
• 150738-45-7 2,4-di-O-acetyl-3-O-methyl-α-L-rhamnopyranose 
• 131675-60-0 3-Iodo-5,6-dimethoxy-4-((2S,3R,4R,5S,6S)-4-methoxy-6-methyl-3,5-bis-triethylsilanyloxy-tetrahydro-pyran-2-yloxy)-2-methyl-thiobenzoic acid S-phenyl ester 
• 131675-33-7 4-((2S,3R,4R,5S,6S)-3,5-Dihydroxy-4-methoxy-6-methyl-tetrahydro-pyran-2-yloxy)-3-iodo-5,6-dimethoxy-2-methyl-thiobenzoic acid S-phenyl ester 

Relevant academic research and scientific papers

Total synthesis of calicheamicin γ1I. 1. Synthesis of the oligosaccharide fragment

The first total synthesis of the calicheamicin γ1I oligosaccharide fragment in the form of its methyl glycoside (62) has been achieved. The synthetic challenge of the B-ring was recognized and studied initially, resulting in a novel and unique solution to the stereochemical problems posed involving a [3,3]-sigmatropic rearrangement of an allylic thionoimidazolide (111). This chemistry was initially worked out on a model for the ABC-ring system (47) and then successfully applied to the real system. The success of this synthesis has enabled the completion of the first synthesis of the natural product itself, calicheamicin γ1I (1), as will be described in the following papers in this issue.