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. Author manuscript; available in PMC: 2018 Jul 6.
Published in final edited form as: J Org Chem. 2018 Mar 5;83(13):7109–7120. doi: 10.1021/acs.joc.8b00094

Table 1.

NMR Data for (ω) and (ω − 2)-Hydroxyacyl Ascarosides (10–12) Isolated from C. nigoni (400 MHz, CD3OD)

threo-asc-7OH-ΔC9 (10) threo-asc-7OH-C9 (11) asc-9OH-ΔC9 (12)
position δCa δHb, mult (J, Hz) δCa δHb, mult (J, Hz) δCa δHb, mult (J, Hz)
1 nd C – nd C – nd C –
2 124.8 CH 5.83 d (15.5) 37.5 CH2 2.21 t (7.6) 122.9 CH 5.81 d (15.6)
3 148.1 CH 6.86 dt (15.5, 7.0) 26.9 CH2 1.63 m 150.7 CH 6.95 dt (15.6, 6.9)
4 32.7 CH2 2.25 m 30.4 CH2 1.40 m 33.1 CH2 2.25 m
5 25.6 CH2 1.54–1.68 m 27.0 CH2 1.40 m 29.3 CH2 1.52 m
6 32.8 CH2 1.48–1.62 m 32.9 CH2 1.48–1.53 m 26.3 CH2 1.50 m
7 74.8 CH 3.53 m 75.2 CH 3.52 m 32.8 CH2 1.59 m
8 75.5 CH 3.74 dq (3.9, 6.3) 75.6 CH 3.73 dq (3.8, 6.2) 78.6 CH 3.69 m
9 14.5 CH3 1.14 d (6.3) 14.6 CH3 1.14 d (6.2) 64.6 CH2 3.50 dd (11.7, 5.6) 3.60 dd (11.7, 4.2)
1′ 97.9 CH 4.65 s 97.8 CH 4.65 s 99.8 CH 4.75 s
2′ 69.7 CH 3.76 s.br 69.8 CH 3.76 s.br 69.6 CH 3.84 s.br
3′ax 35.8 CH2 1.95 dt (13.0, 3.8) 35.8 CH2 1.95 dt (13.0, 3.8) 35.9 CH2 1.95 dt (13.0, 3.8)
3′eq 1.80 ddd (13.0, 11.4, 3.0) 1.81 ddd (13.0, 11.4, 3.0) 1.78 ddd (13.0, 11.2, 3.1)
4′ 68.2 CH 3.52 ddd (11.3, 9.3, 4.3) 68.4 CH 3.51 ddd (11.4, 9.5, 4.4) 68.4 CH 3.53 m
5′ 71.3 CH 3.64 dq (9.3, 6.3) 71.4 CH 3.66 dq (9.5, 6.3) 71.4 CH 3.67 m
6′ 17.8 CH3 1.22 d (6.2) 17.8 CH3 1.22 d (6.2) 18.1 CH3 1.22 d (6.1)
a

From HSQC spectrum.

b

From 1H NMR and dqf-COSY spectra.