Supplementary Dates of Manuscriptoxo-Analogues of 20-Hydroxyecdysone in the Synthesisofnovel

Supplementary dates of manuscriptOxo-analogues of 20-hydroxyecdysone in the synthesisofnovel fluorinated ecdysteroid derivatives

Rimma G. Savchenko*, Anastasia V. Apaeva, Svetlana A. Kostyleva, Oleg S. Mozgovoj, Victor N. Odinokov, Lyudmila V. Parfenova

Fig.S1

1H NMR spectra of (20R,22R)-2β,3β:20,22-Diisopropylidenedioxy-25-oxo-27-nor-5β-cholest-7,14-dien-6-one

Fig.S1

13C NMR spectra of (20R,22R)-2β,3β:20,22-Diisopropylidenedioxy-25-oxo-27-nor-5β-cholest-7,14-dien-6-one

Fig.S2

1H NMR spectra of (20R,22R)-2β,3β:20,22-Diisopropylidenedioxy-24-oxo-25,26,27-trisnor-5β-cholest-7,14-dien-6-one

Fig.S2

13CNMR spectra of (20R,22R)-2β,3β:20,22-Diisopropylidenedioxy-24-oxo-25,26,27-trisnor-5β-cholest-7,14-dien-6-one

Fig.S3

1H NMR spectra of (20R,22R,25R/S)-14α,25-Dihydroxy-2β,3β:20,22-diisopropylidenedioxy-27-nor-5β-cholest-7-en-6-one

Fig.S3

13C NMR spectra of (20R,22R,25R/S)-14α,25-Dihydroxy-2β,3β:20,22-diisopropylidenedioxy-27-nor-5β-cholest-7-en-6-one

1H-1H NOESY spectrum of (20R,22R,25R/S)-14α,25-Dihydroxy-2β,3β:20,22-diisopropylidenedioxy-27-nor-5β-cholest-7-en-6-one (S3)

1H-1H COSY spectrum of (20R,22R,25R/S)-14α,25-Dihydroxy-2β,3β:20,22-diisopropylidenedioxy-27-nor-5β-cholest-7-en-6-one (S3)

1H-13C HSQC spectrum of (20R,22R,25R/S)-14α,25-Dihydroxy-2β,3β:20,22-diisopropylidenedioxy-27-nor-5β-cholest-7-en-6-one (S3)

1H-13C HMBC spectrum of (20R,22R,25R/S)-14α,25-Dihydroxy-2β,3β:20,22-diisopropylidenedioxy-27-nor-5β-cholest-7-en-6(S3)

13C-DEPT spectrum of (20R,22R,25R/S)-14α,25-Dihydroxy-2β,3β:20,22-diisopropylidenedioxy-27-nor-5β-cholest-7-en-6-one(S3)

Fig.S4

1H NMR spectra of (20R,22R)-14α,24-Dihydroxy-2β,3β:20,22-diisopropylidenedioxy-25,26,27-trisnor-5β-cholest-7-en-6-one

13C NMR spectra of (20R,22R)-14α,24-Dihydroxy-2β,3β:20,22-diisopropylidenedioxy-25,26,27-trisnor-5β-cholest-7-en-6-one(S4)

1H-1H COSY spectrum of (20R,22R)-14α,24-Dihydroxy-2β,3β:20,22-diisopropylidenedioxy-25,26,27-trisnor-5β-cholest-7-en-6-one(S4)

1H-13C HSQC spectrum of (20R,22R)-14α,24-Dihydroxy-2β,3β:20,22-diisopropylidenedioxy-25,26,27-trisnor-5β-cholest-7-en-6-one(S4)

1H-13C HMBC spectrum of (20R,22R)-14α,24-Dihydroxy-2β,3β:20,22-diisopropylidenedioxy-25,26,27-trisnor-5β-cholest-7-en-6-one(S4)

Fig.S5

1H NMR spectra ofR-MPA ester of (20R,22R,25R/S)-14α,25-Dihydroxy-2β,3β:20,22-diisopropylidenedioxy-27-nor-5β-cholest-7-en-6-one (S5)

13C NMR spectra of R-MPA ester of (20R,22R,25R/S)-14α,25-Dihydroxy-2β,3β:20,22-diisopropylidenedioxy-27-nor-5β-cholest-7-en-6-one(S5)

1H-1H NOESY spectrum of R-MPA ester of (20R,22R,25R/S)-14α,25-Dihydroxy-2β,3β:20,22-diisopropylidenedioxy-27-nor-5β-cholest-7-en-6-one (S5)

1H-1H COSY spectrum of R-MPA ester of (20R,22R,25R/S)-14α,25-Dihydroxy-2β,3β:20,22-diisopropylidenedioxy-27-nor-5β-cholest-7-en-6-one (S5)

1H-13C HSQC spectrum of R-MPA ester of (20R,22R,25R/S)-14α,25-Dihydroxy-2β,3β:20,22-diisopropylidenedioxy-27-nor-5β-cholest-7-en-6-one (S5)

1H-13C HMBC spectrum of R-MPA ester of (20R,22R,25R/S)-14α,25-Dihydroxy-2β,3β:20,22-diisopropylidenedioxy-27-nor-5β-cholest-7-en-6-one(S5)

13C-DEPT spectrum of R-MPA ester of (20R,22R,25R/S)-14α,25-Dihydroxy-2β,3β:20,22-diisopropylidenedioxy-27-nor-5β-cholest-7-en-6-one(S5)

Fig.S6

1H NMR spectra of (20R,22R)-2β,3β:20,22-Diisopropylidenedioxy-25-fluoro-27-nor-5β-cholest-7,14-dien-6-one(S6)

13C NMR spectra of (20R,22R)-2β,3β:20,22-Diisopropylidenedioxy-25-fluoro-27-nor-5β-cholest-7,14-dien-6-one(S6)

1H-1H COSY spectrum of (20R,22R)-2β,3β:20,22-Diisopropylidenedioxy-25-fluoro-27-nor-5β-cholest-7,14-dien-6-one(S6)

1H-13C HSQC spectrum of (20R,22R)-2β,3β:20,22-Diisopropylidenedioxy-25-fluoro-27-nor-5β-cholest-7,14-dien-6-one(S6)

1H-13C HMBC spectrum of (20R,22R)-2β,3β:20,22-Diisopropylidenedioxy-25-fluoro-27-nor-5β-cholest-7,14-dien-6-one(S6)

13C-DEPT spectrum of (20R,22R)-2β,3β:20,22-Diisopropylidenedioxy-25-fluoro-27-nor-5β-cholest-7,14-dien-6-one(S6)

19F NMR spectra of (20R,22R)-2β,3β:20,22-Diisopropylidenedioxy-25-fluoro-27-nor-5β-cholest-7,14-dien-6-one(S6)

Fig.S7

1H NMR spectra of (20R,22R)-2β,3β:20,22-Diisopropylidenedioxy-24-fluoro-25,26,27-trisnor-5β-cholest-7,14-dien-6-one(S7)

13C NMR spectra of (20R,22R)-2β,3β:20,22-Diisopropylidenedioxy-24-fluoro-25,26,27-trisnor-5β-cholest-7,14-dien-6-one(S7)

19F NMR spectra of (20R,22R)-2β,3β:20,22-Diisopropylidenedioxy-24-fluoro-25,26,27-trisnor-5β-cholest-7,14-dien-6-one(S7)

Fig.S8

1H NMR spectra of (20R,22R)-2β,3β:20,22-Diisopropylidenedioxy-24-fluoro-25,26,27-trisnor-5β-cholest-8,14-dien-6-one

13C NMR spectra of (20R,22R)-2β,3β:20,22-Diisopropylidenedioxy-24-fluoro-25,26,27-trisnor-5β-cholest-8,14-dien-6-one

19F NMR spectra of (20R,22R)-2β,3β:20,22-Diisopropylidenedioxy-24-fluoro-25,26,27-trisnor-5β-cholest-8,14-dien-6-one