Spektraris NMR
2α-Hydroxy-7β,9α,10β,13α-tetraacetoxy-5α-(2'-hydroxy-3'-N,N- dimethylamino-3'-phenyl)propionyloxytaxa-4(20),11-diene
Common Name: 2α-Hydroxy-7β,9α,10β,13α-tetraacetoxy-5α-(2'-hydroxy-3'-N,N- dimethylamino-3'-phenyl)propionyloxytaxa-4(20),11-diene
Synonyms:
CAS Registry Number: 824951-59-9
InChI: InChI=1S/C39H53NO12/c1-19-28(52-37(47)34(46)32(40(10)11)25-15-13-12-14-16-25)18-29(49-22(4)42)39(9)30(19)33(45)26-17-27(48-21(3)41)20(2)31(38(26,7)8)35(50-23(5)43)36(39)51-24(6)44/h12-16,26-30,32-36,45-46H,1,17-18H2,2-11H3/t26-,27-,28-,29-,30-,32-,33+,34+,35+,36-,39+/m0/s1
InChIKey: InChIKey=BJLQEOZFLGIDER-HQQKRINVSA-N
Formula: C39H53N1O12
Molecular Weight: 727.84
Exact Mass: 727.3568
NMR Solvent: acetone-d6
MHz: 500.0
Calibration: solvent residue 2.04 and 29.8 ppm for proton and carbon respectively.
NMR references: Shi, Q., Ji, X., Lesimple, A., Sauriol, F., and Zamir, L.O. (2004). Taxanes with C-5-amino-side chains from the needles of Taxus canadensis. Phytochemistry 65, 3097–3106.
Species: Taxus
Notes: Coupling constant (J) not reported for doublet at 2.78ppm (H-3) due to overlap reported in reference. A number of coupling constants are reported as approximate. See reference for further details. Carbon at position 4 is missing.
Proton NMR Peaks
| Position | PPM | Peak Type | J (Hz) |
|---|---|---|---|
| 1 | 2.06 | m | |
| 2 | 4.26 | td | 6.5, 1.9 |
| 2-OH | 3.52 | d | 6.5 |
| 3 | 2.78 | d | |
| 5 | 5.15 | td | 2.7 |
| 6a | 1.55 | m | |
| 6b | 0.85 | br | |
| 7 | 5.29 | br dd | 10.8, 4.3 |
| 9 | 5.8 | d | 10.8 |
| 10 | 6.16 | d | 10.8 |
| 13 | 5.91 | br t | 9 |
| 14a | 2.44 | dt | 15.2, 9.7 |
| 14b | 1.43 | m | |
| 16 | 1.12 | s | |
| 17 | 1.66 | s | |
| 18 | 2.24 | s | |
| 19 | 0.95 | s | |
| 20a | 5.82 | s | |
| 20b | 5.35 | s | |
| OAc | 2.07 | s | |
| OAc | 2.03 | s | |
| OAc | 2.02 | s | |
| OAc | 1.94 | s | |
| 2' | 3.93 | br | |
| 3' | 4.77 | br | |
| Ph-o | 7.45 | br | |
| Ph-m | 7.38 | t | 7.2 |
| Ph-p | 7.31 | t | |
| N-Me2 | 2.3 | br |
Carbon NMR Peaks
| Position | PPM |
|---|---|
| 1 | 52.1 |
| 2 | 68.7 |
| 3 | 43.9 |
| 5 | 76.8 |
| 6 | 34.3 |
| 7 | 69.6 |
| 8 | 46.8 |
| 9 | 75.5 |
| 10 | 71.4 |
| 11 | 132.7 |
| 12 | 136.6 |
| 13 | 69.9 |
| 14 | 27.6 |
| 15 | 37.5 |
| 16 | 30.8 |
| 17 | 27 |
| 18 | 14.7 |
| 19 | 13 |
| 20 | 121.3 |
| OAc | 19.8 |
| OAc | 170.2 |
| OAc | 20.4 |
| OAc | 168.5 |
| OAc | 19.7 |
| OAc | 169.4 |
| OAc | 19.8 |
| OAc | 168.1 |
| 3' | 71.3 |
| Ph-o | 130.1 |
| Ph-m | 128.2 |
| Ph-p | 128 |
| N-Me2 | 41.3 |
