359849-32-4

Upstream product

• 359849-08-4 tert-butyl (4S)-5-hydroxy-2,4-dimethylpent-2-enoate 
• 359849-14-2 tert-butyl (2R,3R,4R)-3,5-dihydroxy-2,4-dimethylpentanoate 
• 359849-11-9 tert-butyl 2R-(5R-methyl-2-oxo[1,3]dioxan-4R-yl)propionate 
• 359849-16-4 tert-butyl (2R)-2-[(4R,5R)-2,2,5-trimethyl[1,3]dioxan-4-yl]propionate 
• 359849-05-1 tert-butyl (4S)-5-carbamoyloxy-2,4-dimethylpent-2-enoate 
• 359849-06-2 tert-butyl 2R-2-iodo-[(4R,5R)-5-methyl-2-oxo[1,3]dioxan-4-yl]propionate 
• 359849-29-9 (3R,4R,5S,6R)-6-[(1R)-2-(tert-butyldiphenylsilyloxy-1-methylethyl)]-4-hydroxy-3,5-dimethyltetrahydropyran-2-one 
• 359849-25-5 tert-butyl (2R)-2-[(4R,5R,6R)-6-[(1R)-2-tert-butyldiphenylsilyloxy-1-methylethyl]-5-methyl-2-oxo[1,3]dioxan-4-yl]-2-iodopropionate 
• 359849-27-7 tert-butyl (2R)-2-[(4R,5R,6R)-6-[(1R)-2-tert-butyldiphenylsilyloxy-1-methylethyl]-5-methyl-2-oxo[1,3]dioxan-4-yl]propionate 
• 359849-10-8 tert-butyl 2R-2-phenylseleno-[(4R,5R)-5-methyl-2-oxo[1,3]dioxan-4-yl]propionate 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 76123-21-2 (2R)-2-[(4R,5R)-2,2,5-trimethyl[1,3]dioxan-4-yl]propionaldehyde 
• 76156-31-5 (S)-2-((4S,5R)-2,2,5-Trimethyl-[1,3]dioxan-4-yl)-propan-1-ol 
• 77-76-9 2,2-dimethoxy-propane 

Downstream Products

• 207226-48-0 (2S,3R)-2-[(4S,5R,6R)-6-[(1R)-2-tert-butyldiphenylsilyloxy-1-methylethyl]-2,2,5-trimethyl[1,3]dioxan-4-yl]-5-[1,3]dioxolanepentan-3-ol 
• 114597-34-1 (2S,3R)-3-benzyloxymethoxy-2-[(4S,5R,6R)-6-[(1R)-2-tert-butyldiphenylsilyloxy-1-methylethyl]-2,2,5-trimethyl[1,3]dioxan-4-yl]-5-[1,3]dioxolanepentane 

Relevant academic research and scientific papers

Cyclofunctionalization and free-radical-based hydrogen-transfer reactions. An iterative reaction sequence applied to the synthesis of the C7-C16 subunit of zincophorin

The strategy considered herein features an iodocyclofunctionalization/hydrogen-transfer reaction sequence for the elaboration of propionate motifs. Proceeding with excellent yield and diastereo-selectivity, the synthetic sequence proposed gives access to the anti-anti dipropionate motif when the reduction step is performed under the control of the exocyclic effect. The tandem sequence is applied successfully to the synthesis of the C7-C16 subunit of zincophorin, and iteration of the process gives the desired anti-anti-anti-anti polypropionate stereopentad. Modifications of the reaction sequence - including phenylselenocyclofunctionalization, carbonate hydrolysis, and chelation-controlled radical reduction reactions - lead to the formation of the anti-syn dipropionate motif with remarkable diastereocontrol.