Methyl 5-deoxy-5-iodo-pentofuranoside

After establishing general reaction conditions for the zinc-mediated reductive ring-opening-allylation of iodoglycosides, Madsen et al. developed a similar procedure for the domino reaction of methyl 5-deoxy-5-iodo-pentofuranosides with propargyl... 

Methyl 2,4-di-0-benzoyl-3-deoxy-3-iodo-p-L-ribopyranoside, D-271 Methyl 2,5-di-0-benzoyl-3-deoxy-a-D-/Areo-pentofuranoside, D-349 Methyl 4,6-di-0-benzoyl-2,3-dideoxy-a-D-er /Aro-hex-2-enopyranoside, D-584... 

For example, Madsen et al. reported a short synthetic strategy for preparation of conduritols, using as a key step a domino zinc-mediated liragmentation/allylation of protected methyl 5-deoxy-5-iodo-D-pentofuranosides followed by ring-closing olefin metathesis [39]. Thus, methyl furanoside 3 and 3-bromopropenyl acetate were treated with zinc in a THF/H2O mixture under sonication at 40°C. This resulted in one major product 14, which was isolated in a 72% yield as a 4 1 mixture of two isomers. Conduritol D (16) was obtained from diene 14 when this compound was subjected to RCM followed by deprotection (Scheme 3.8). 

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See also in sourсe #XX -- [ ]

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