REGIOSELECTIVE 1-N-ALKYLATION AND REARRANGEMENT OF ADENOSINE
DERIVATIVES
(Supporting information)
Vladimir E. Oslovsky, Mikhail S. Drenichev, Sergey N. Mikhailov
Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Vavilov str. 32, Moscow
119991, Russian Federation
1
H and 13C (with complete proton decoupling) NMR spectra were recorded on Bruker AMX 400 NMR
instrument at 300 K relative to the residual solvent signals as internal standards (CDCl3, 1H: δ = 7.26,
13C: δ = 77.16; DMSO-d6, 1H: δ = 2.50, 13C: δ = 39.52; CD3OD, 1H: δ = 3.31, 13C: δ = 49.00).
1
H-NMR-spectra were recorded at 400 MHz and 13C-NMR-spectra at 100 MHz.
1
H-NMR-spectrum (400 MHz) of 3′,5′-di-O-acetyl-2′-deoxyadenosine (2)
in DMSO-d6 at 300 K
13
C-NMR-spectrum (100 MHz) of 3′,5′-di-O-acetyl-2′-deoxyadenosine (2)
in CDCl3 at 300 K
1
H-NMR-spectrum (400 MHz) of 1N-Methyl-2′,3′,5′-tri-O-acetyladenosine iodohydrate (3a)
in CDCl3 at 300 K
1
H-NMR-spectrum (400 MHz) of 1N-Benzyl-2′,3′,5′-tri-O-acetyladenosine (3b)
in CDCl3 at 300 K
1
H-NMR-spectrum (400 MHz) of 1N-(3-Methyl-2-buten-1-yl)-2′,3′,5′-tri-O-acetyladenosine (3c)
in CDCl3 at 300 K
1
H-NMR-spectrum (400 MHz) of 1N-Methyl-3′,5′-di-O-acetyl-2′-deoxyadenosine iodohydrate (4a)
in CD3OD with addition of chloroform-d (singlet at 7.88 ppm) at 300 K
1
H-NMR-spectrum (400 MHz) of 1N-Benzyl-3′,5′-di-O-acetyl-2′-deoxyadenosine (4b)
in CDCl3 at 300 K
1
H-NMR-spectrum (400 MHz) of 1N-(3-Methyl-2-buten-1-yl)-3′,5′-di-O-acetyl-2′-deoxyadenosine (4c)
in CDCl3 at 300 K
1
H-NMR-spectrum (400 MHz) of N6-Benzyl-2′-deoxyadenosine (6b)
in DMSO-d6 at 300 K
13
C-NMR-spectrum (100 MHz) of N6-Benzyl-2′-deoxyadenosine (6b)
in DMSO-d6 at 300 K
1
H-NMR-spectrum (400 MHz) of N6-(3-Methyl-2-buten-1-yl)-2′-deoxyadenosine (6c)
in DMSO-d6 at 300 K
13
C-NMR-spectrum (100 MHz) of N6-(3-Methyl-2-buten-1-yl)-2′-deoxyadenosine (6c)
in DMSO-d6 at 300 K
1
H-NMR-spectrum (400 MHz) of 1N-Benzyladenosine chlorohydrate (7b)
in DMSO-d6 at 300 K
13
C-NMR-spectrum (100 MHz) of 1N-Benzyladenosine chlorohydrate (7b)
in DMSO-d6 at 300 K
1
H-NMR-spectrum (400 MHz) of 1N-(3-methyl-2-buten-1-yl)-adenosine chlorohydrate (7c)
in DMSO-d6 at 300 K
13
C-NMR-spectrum (100 MHz) of 1N-(3-methyl-2-buten-1-yl)-adenosine chlorohydrate (7c)
in DMSO-d6 at 300 K
1
H-NMR-spectrum (400 MHz) of 1N-benzyl-2′-deoxyadenosine chlorohydrate (8b)
in DMSO-d6 at 300 K
13
C-NMR-spectrum (100 MHz) of 1N-benzyl-2′-deoxyadenosine chlorohydrate (8b)
in DMSO-d6 at 300 K
1
H-NMR-spectrum (400 MHz) of 1N-(3-methyl-2-buten-1-yl)-2′-deoxyadenosine chlorohydrate (8c)
in CDCl3 at 300 K
13
C-NMR-spectrum (100 MHz) of 1N-(3-methyl-2-buten-1-yl)-2′-deoxyadenosine chlorohydrate (8c)
in DMSO-d6 at 300 K
1
H-NMR-spectrum (400 MHz) of 1-N-Benzyl-N6-acetyl-2′,3′,5′-tri-O-acetyladenosine (10b)
in DMSO-d6 at 300 K
13
C-NMR-spectrum (100 MHz) of 1-N-Benzyl-N6-acetyl-2′,3′,5′-tri-O-acetyladenosine (10b)
in DMSO-d6 at 300 K
HSQC-spectrum of 1-N-Benzyl-N6-acetyl-2′,3′,5′-tri-O-acetyladenosine (10b)
in DMSO-d6 at 300 K
HMBC-spectrum of 1-N-Benzyl-N6-acetyl-2′,3′,5′-tri-O-acetyladenosine (10b)
in DMSO-d6 at 300 K
NOESY-spectrum of 1-N-Benzyl-N6-acetyl-2′,3′,5′-tri-O-acetyladenosine (10b)
in DMSO-d6 at 300 K
HMBC-spectrum of N6-Benzyl-N6-acetyl-2′,3′,5′-tri-O-acetyladenosine
in DMSO-d6 at 300 K
NOESY-spectrum of N6-Benzyl-N6-acetyl-2′,3′,5′-tri-O-acetyladenosine
in DMSO-d6 at 300 K
1
H-NMR spectrum (400 MHz) of 1-N-(3-Methyl-2-buten-1-yl)-N6-acetyl-2′,3′,5′-tri-O-acetyladenosine
(10c)
in CDCl3 at 300 K
13
C-NMR spectrum (100 MHz) of 1-N-(3-Methyl-2-buten-1-yl)-N6-acetyl-2′,3′,5′-tri-O-acetyladenosine
(10c)
in CDCl3 at 300 K
1
H-NMR-spectrum (400 MHz) of 1-N-(Prop-2-ynyl)-N6-acetyl-2′,3′,5′-tri-O-acetyladenosine (10d)
in CDCl3 at 300 K
13
C-NMR-spectrum (100 MHz) of 1-N-(Prop-2-ynyl)-N6-acetyl-2′,3′,5′-tri-O-acetyladenosine (10d)
in CDCl3 at 300 K
1
H-NMR-spectrum (400 MHz) of 1-N-(3-Phenylpropan-1-yl)-N6-acetyl-2′,3′,5′-tri-O-acetyladenosine
(10e)
in CDCl3 at 300 K
13
C-NMR-spectrum (100 MHz) of 1-N-(3-Phenylpropan-1-yl)-N6-acetyl-2′,3′,5′-tri-O-acetyladenosine
(10e)
in CDCl3 at 300 K
1
H-NMR-spectrum (400 MHz) of 1-N-Benzyl-N6-acetyl-3′,5′-di-O-acetyl-2′-deoxyadenosine (12b)
in DMSO-d6 at 300 K
13
C-NMR-spectrum (100 MHz) of 1-N-Benzyl-N6-acetyl-3′,5′-di-O-acetyl-2′-deoxyadenosine (12b)
in DMSO-d6 at 300 K
1
H-NMR-spectrum (400 MHz) of 1-N-(3-Methyl-2-buten-1-yl)-N6-acetyl-3′,5′-di-O-acetyl-2′deoxyadenosine (12c)
in DMSO-d6 at 300 K
13
C-NMR-spectrum (100 MHz) of 1-N-(3-Methyl-2-buten-1-yl)-N6-acetyl-3′,5′-di-O-acetyl-2′deoxyadenosine (12c)
in DMSO-d6 at 300 K
1
H-NMR-spectrum (400 MHz) of N6-(3-Phenylpropan-1-yl)-adenosine (5e)
in DMSO-d6 with addition of MeOH (singlet at 3.15 ppm) at 300 K
13
C-NMR-spectrum (100 MHz) of N6-(3-Phenylpropan-1-yl)-adenosine (5e)
in DMSO-d6 at 300 K