The cis-configuration of 1,2-cyclohexanediol was determined directly from the zero optical rotation of the
organic phase, becausep-coumaric acid is optically inactive. 18 The absolute configuration of8at C-1 was determined from
the chemical shift of the anomeric carbon in the 13C NMR spectrum. In both the trans and cis forms of 1,2-cyclohexanediol-1-O-β-D-glucopyranoside, the chemical shifts of the anomeric carbon of the 1R forms occur more up field sh ifted than those of the 1S forms.13−15 Compound 8 showed a moreup field shifted anomeric carbon signal (δC101.1) than that of10(δC102.3) (see below), which was assigned as a C-1 and C-2 diastereomer of 8. Thus, compound 8 was assigned with a 1R
configuration and was established as (1R,2S)-2-hydroxycyclo-hexyl-2′-O-cis-p-coumaroyl-β-D-glucopyranoside