Spektraris NMR
7-Xylosyl-10-deacetyltaxol
Common Name: 7-Xylosyl-10-deacetyltaxol
Synonyms: 10-Deacetyl-7-xylosyltaxol
CAS Registry Number: 90332-63-1
InChI: InChI=1S/C50H57NO17/c1-25-31(65-45(61)38(56)35(27-15-9-6-10-16-27)51-43(59)28-17-11-7-12-18-28)22-50(62)42(67-44(60)29-19-13-8-14-20-29)40-48(5,41(58)37(55)34(25)47(50,3)4)32(21-33-49(40,24-64-33)68-26(2)52)66-46-39(57)36(54)30(53)23-63-46/h6-20,30-33,35-40,42,46,53-57,62H,21-24H2,1-5H3,(H,51,59)/t30-,31+,32+,33-,35+,36+,37-,38-,39-,40+,42+,46+,48-,49+,50-/m1/s1
InChIKey: InChIKey=ORKLEZFXASNLFJ-DYLQFHMVSA-N
Formula: C50H57N1O17
Molecular Weight: 943.98
Exact Mass: 943.3626
NMR Solvent: dimethyl sulfoxide-d6; acetone-d6
MHz: 400.0
Calibration: TMS for proton, carbon not mentioned.
NMR references: Sénilh, V., Blechert, S., Colin, M., Guénard, D., Picot, F., Potier, P., and Varenne, P. (1984). Mise en Évidence de Nouveaux Analogues du Taxol Extraits de Taxus baccata. J. Nat. Prod. 47, 131–137.
Shi, Q.-W., Petzke, T.L., Sauriol, F., Mamer, O., and Zamir, L.O. (2003). Taxanes in rooted cuttings vs. mature Japanese yew. Canadian Journal of Chemistry 81, 64–74.
Species: Taxus
Notes: Reference article in for proton data in French language. Positions with '' refer to protons on xylosyl side chain. See literature for further details. Carbon NMR data in Shi et al., 2003.
Proton NMR Peaks
| Position | PPM | Peak Type | J (Hz) |
|---|---|---|---|
| 2 | 5.65 | d | 7 |
| 3 | 3.89 | d | 7 |
| 5 | 4.95 | dd | 9 |
| 6 | 1.98 | m | |
| 6 | 2.7 | m | |
| 7 | 4.14 | m | |
| 10 | 5.33 | s | |
| 13 | 6.19 | t | 9 |
| 14 | 2.22 | m | |
| 16 | 1.19 | s | |
| 17 | 1.12 | s | |
| 18 | 1.91 | s | |
| 19 | 1.77 | s | |
| 20 | 4.23 | d | 9 |
| 20 | 4.27 | d | 9 |
| OAc | 2.42 | ||
| 2' | 4.72 | d | 3 |
| 3' | 5.76 | dd | 9, 3 |
| 3' Ph | 7.45 | ||
| NH | 8.26 | d | 9 |
| 1'' | 4.1 | d | 7 |
| 2'' | 3.2 | m | |
| 3'' | 3.4 | t | 8 |
| 4'' | 3.5 | m | |
| 5'' | 3.2 | m | |
| 5'' | 3.8 | m |
Carbon NMR Peaks
| Position | PPM |
|---|---|
| 1 | 77.6 |
| 2 | 74.7 |
| 3 | 46.6 |
| 4 | 80.1 |
| 5 | 83.8 |
| 6 | 35.6 |
| 7 | 81.4 |
| 8 | 56.3 |
| 9 | 209.7 |
| 10 | 74.6 |
| 11 | 136 |
| 12 | 137.3 |
| 13 | 70.9 |
| 14 | 36 |
| 15 | 42.9 |
| 16 | 26.1 |
| 17 | 20.3 |
| 18 | 13.6 |
| 19 | 10.1 |
| 20 | 75.7 |
| OAc | 22.1 |
| OAc | 170.1 |
| OBz-2 | 165.6 |
| C1-o | 12.9 |
| C1-o | 165.6 |
| C1-p | 128.5 |
| C1-m | 133 |
| p | 133 |
| 1' | 172.7 |
| 2' | 73.8 |
| 3' | 56 |
| 5' CO | 166.5 |
| Ph 6' o | 127.1 |
| Ph 6' o | 166.5 |
| Ph 6' m | 128.2 |
| Ph 6' p | 131 |
| Ph 3' | 139.2 |
| Ph 3' o | 127.2 |
| Ph 3' m | 128.3 |
| Ph 3' p | 127.2 |
| Sugar 1" | 105.1 |
| 2" | 73.3 |
| 3" | 76.2 |
| 4" | 69.4 |
| 5" | 65.4 |
