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. Author manuscript; available in PMC: 2018 Nov 1.
Published in final edited form as: J Med Chem. 1999 May 6;42(9):1625–1638. doi: 10.1021/jm980657j

Table 3.

Synthetic Data for Nucleotide Derivatives, Including Structural Verification Using HRMS and Purity Verification Using HPLC

FAB (M - H+)
 HPLC tR, mina
compd formula calcd found system A system B yields, %b
1 C10H15O9N5P2 410.0267 410.0249 5.98 11.51 44
2 C11H17O9N5P2 424.0423 424.0404 6.93 12.32 41
3 C10H15O10N5P2 426.0216 426.0226 6.12 10.51 15
4 C12H18O9N4P2 423.0471 423.0479 8.49 10.64 19
5 C10H14O9N5P2Q 443.9877 443.9872 7.20 12.14 58
6 CUH16O9N5P2Cl 458.0034 458.0035 8.51 11.42 17
7 C11H16O9N5P2I 549.9390 549.9396 7.84 8.40 16
8 C11H17O10N5P2 440.0372 440.0358 6.32 10.13 23
9 C11H17O9N5P2S 456.0144 456.0122 8.14 12.98 48
10 C12H19O9N5P2S 470.0301 470.0307 9.99 12.07 17
11 C12H19O9N5P2S 470.0301 470.0307 8.94 9.84 23
12 C13H21O9N5P2S 484.0457 484.0453 10.49 11.81 23
13 C13H21O9N5P2S 484.0457 484.0452 7.77 11.65 21
14 C14H23O9N5P2S 498.0614 498.0605 9.75 12.40 10
15 C14H21O9N5P2S 496.0457 496.0445 9.20 12.35 13
16 C17H29O9N5P2S 540.1083 540.1057 12.87 15.11 25
17a C11H18O9N6P2 439.0532 439.0535 6.48 7.15 19
17b C10H15O10N5P2 426.0216 426.0216 9.28 9.69 39
18 C11H17O9N5P2 424.0423 424.0412 6.07 8.72 9
19 C12H17O9N5P2 436.0423 436.0429 6.43 9.00 13
20 C11H17O10N5P2 440.0372 440.0380 4.14 7.28 17
21 C11H17O9N5P2S 456.0144 456.0160 6.89 8.23 37
22 C11H18O9N6P2 439.0532 439.0497 6.67 9.20 5
23 C10H15O8N5P2S 426.0038 426.0051 6.75 8.92 13
24 C11H17O8N5P2 408.0474 408.0474 5.97 7.04 24
25 C12H20O8N6P2 437.0740 437.0759 3.70 5.21 10
26 C10H14O6N5PS 362.0324 362.0319 2.76 7.63 2
27 C11H17O9N5P2 424.0423 424.0432 7.04 7.37 10
28 C12H19O9N5P2 438.0580 438.0580 3.06 4.48 22
29a C11H15O8N5P2 406.0318 406.0336 7.60 7.47 20
29b C11H17O14N5P4 565.9644 565.9664 6.91 12.11 5
30 C10H14O9N8P2 451.0281 451.0288 3.70 5.78 13
31 C10H16O15N8P4 610.9607 610.9602 3.81 5.99 3
32 C9H14O11N2P2 386.9995 386.9977 4.20 9.85 39
33 C10H16O11N2P2 401.0151 401.0160 4.63 9.73 39
34 C9H13O11N2P2F 404.9889 404.9901 3.66 7.83 27
35 C9H15O10N3P2 386.0154 386.0136 2.10 3.34 36
36 C11H17O9N5P2 424.0423 424.0423 4.31 7.56 1
a

Purity of each derivative was 95%, as determined using HPLC (Hewlett-Packard 1090) with two different mobile phases, using an SMT OD-5–60 RP-C18 column (250 × 4.6 mm; Separation Methods Technologies, Inc., Newark, DE). The flow rate was 1 mL/min, with a typical pressure of 100 bar. System A: linear gradient solvent system, 0.1 M TEAA/CH3CN from 95/5 to 40/60 in 20 min. System B: linear gradient solvent system, 5 mM TBAP/CH3CN from 80/20 to 40/60 in 20 min.

b

The percent yields refer to phosphorylation reactions