Journal of Organic Chemistry p. 9662 - 9674 (2017)
Update date:2022-08-29
Topics:
Zhang, Pengfei
Hevey, Rachel
Ling, Chang-Chun
The 6-deoxy-β-d-ido-heptopyranoside related to the capsular polysaccharides of C. jejuni HS:4 is very remarkable, owing to the unique, multifaceted structural features that have been combined into one molecule, which include (1) the rare ido-configuration, (2) the unusual 7-carbon backbone, and (3) the challenging β-(1→2)-cis-anomeric configuration. Two distinct strategies toward the total synthesis of this interesting target are reported. The first involved establishment of the β-d-idopyranosyl configuration from β-d-galactopyranosides, prior to a C-6-homologation extending the d-hexose to the desired 6-deoxy-d-heptose. However, this approach encountered difficulties due to the significantly reduced reactivity of the 6-position of the β-d-idopyranosides, so instead a second strategy was employed, which involved first carrying out a 6-homologation on the less flexible d-galactopyranose, followed by a very successful conversion to the desired β-d-ido-configuration found in the target heptopyranoside (2). This report is the first successful synthesis of the 6-deoxy-β-d-ido-heptopyranoside, which could possess interesting immunological properties.
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Doi:10.1271/bbb.70724
(2008)Doi:10.1021/j100181a053
(1992)Doi:10.1016/S0040-4020(01)82158-X
(1966)Doi:10.1021/ja9710058
(1997)Doi:10.1039/c29690000148
(1969)Doi:10.1007/BF00963484
(1991)