The Journal of Organic Chemistry
Note
(d, 2JCP = 8.7 Hz, arom ipso-C), 146.7 (C-6), 129.7 (d, 4JCP = 1.0 Hz, 2
arom m-CH), 125.5 (arom p-CH), 120.1 (d, 3JCP = 4.1 Hz, 2 arom o-
CH), 94.3 (C-5), 73.3 (d, 3JCP = 5.2 Hz, CHO), 71.6 (d, 2JCP = 7.5 Hz,
ACKNOWLEDGMENTS
■
This work was supported by Grant Nos. AI061457, AI056864,
and AI091216 from the National Institutes of Health.
1
CH2OP), 62.1 (d, JCP = 146.2 Hz, CH2P), 48.2 ppm (CH2N); 31P
NMR (162 MHz, CD3OD) δ = 11.28 ppm.
9-[[(5S)-2-Oxido-2-phenoxy-1,4,2-dioxaphosphinan-5-yl]-
methyl]-9H-purin-6-amine (6). The (Rp)-6 diastereomer was
obtained by recrystallization from i-PrOH/EtOAc: 1H NMR (600
MHz, CD3OD) δ = 8.24 (s, 1H, 2-H), 8.13 (s, 1H, 8-H), δ 7.41−7.38
(m, 2H, 2 arom m-CH), 7.26−7.24 (m, 1H, arom p-CH), 7.19−7.17
(m, 2H, 2 arom o-CH), 4.61 (ddd, 3JHP = 17.6 Hz, Jgem = 11.6 Hz, J =
2.0 Hz, 1H, CHAHBO), 4.46 (dd, J = 14.4, 2.9 Hz, 1H, CHHN), 4.42
REFERENCES
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(ddd, Jgem = 11.6, JHP = 1.2 Hz, CHAHBO), 4.39−4.33 (m, 3H,
2
CHHN, CHCHDP, CHXO), 4.10 ppm (dd, Jgem = 15.3 Hz, JHP = 1.4
Hz, 1H, CHCHDP); 13C NMR (126 MHz, CD3OD) 156.05 (C-NH2),
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(arom p-CH), 119.90 (d, JCP = 4.3 Hz, 2 arom o-CH), 118.33
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(NCCCNN), 73.90 (d, JCP = 5.5 Hz, CHO), 72.96 (d, JCP = 9.1
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1
CH3CN: H NMR (600 MHz, CD3OD) δ = 8.20 (s, 1H, 2-H), 8.11
(s, 1H, 8-H), δ 7.38−7.35 (m, 2H, 2 arom m-CH), 7.23−7.21 (m, 1H,
arom p-CH), 7.19−7.17 (m, 2H, 2 arom o-CH), 4.71 (ddd, J = 12.1
Hz, J = 2.8 Hz, 1H, CHAHBO), 4.54 (dd, J = 15.1, 8.8 Hz, 1H,
CHAHBN), 4.50 (m, 1H, CHAHBO), 4.46 (dd, J = 15.0, 7.0, 1H,
CHCHDP), 4.44 (dd, J = 14.7, 3.5 Hz, 1H, CHHN), 4.32 (m, CHXO),
4.15 ppm (dd, J = 14.8, 4.0 Hz, CHCHDP); 13C NMR (126 MHz,
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118.37 (NCCCNN), 72.97 (d, 3JCP = 5.3 Hz, CHO), 71.42 (d, 2JCP
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1
= 7.4 Hz, CH2OP), 61.47 (d, JCP = 145.8 Hz, CH2P), 42.16 ppm
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Union Road, Cambridge, CB21EZ, UK (fax: +44−1233−336033; e-
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ASSOCIATED CONTENT
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S
* Supporting Information
Characterization (NMR, LC-MS, X-ray crystallographic data)
for cyclic (S)-HPMPC and (S)-HPMPA phenyl diesters 5 and
6. This material is available free of charge via the Internet at
(25) Krylov, I. S.; Peterson, L. W.; Kashemirov, B. A.; Breitenbach, J.;
Borysco, K.; Drach, J. C.; Kim, J. S.; Hilfinger, J. M.; McKenna, C. E.
Antiviral Res. 2009, 82, A75−A75.
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AUTHOR INFORMATION
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Corresponding Author
*Phone: +1 213 740 7007. Fax: +1 213 740 0930. E-mail:
688
dx.doi.org/10.1021/jo201735f | J. Org. Chem. 2012, 77, 684−689