Incidence and avoidance of stereospecific 1,2-ethylthio group migration during the synthesis of ethyl 1-thio-α-L-rhamnopyranoside 2,3-orthoester

Article abstract of DOI:10.1016/0008-6215(91)84041-C

The 1,2-migration of an ethylthio group with inversion of configuration at the C-1 and C-2 atoms was observed during the attempted preparation of 2,3-orthoester derivatives of ethyl 1-thio-α-L-rhamnopyranoside. The rearrangement leading to the formation o