19-​Acetoxytaxagifine

19-​Acetoxytaxagifine

Common Name: 19-​Acetoxytaxagifine

Synonyms: Taxezopidine L

CAS Registry Number: 219749-76-5

InChI: InChI=1S/C39H46O15/c1-20-28(54-31(46)15-14-26-12-10-9-11-13-26)17-30(50-22(3)41)38(19-48-21(2)40)32(20)33(51-23(4)42)27-16-29(45)37(8)39(47,36(27,7)18-49-37)35(53-25(6)44)34(38)52-24(5)43/h9-15,27-28,30,32-35,47H,1,16-19H2,2-8H3/b15-14+/t27-,28-,30-,32-,33+,34-,35-,36-,37+,38+,39-/m0/s1

InChIKey: InChIKey=YJLKXWCZWJGUAN-OILLXYFHSA-N

Formula: C39H46O15

Molecular Weight: 754.77

Exact Mass: 754.2837

NMR Solvent: CDCl3

MHz: 400.0

Calibration: TMS

NMR references: Fukushima, M., Takeda, J., Fukamiya, N., Okano, M., Tagahara, K., Zhang, S.-X., Zhang, D.-C., and Lee, K.-H. (1999). A New Taxoid, 19-Acetoxytaxagifine, from Taxus chinensis. J. Nat. Prod. 62, 140–142.

Species: Taxus

Notes: Aromatic protons not fully assigned. Carbons at ortho and meta positions on aromatic ring reported as interchangeable.

Proton NMR Peaks

Position PPM Peak Type J (Hz)
1 2.53 m
2 6.18 m
3 3.47 d 9.6
5 5.37 m
6α 2.37 m
6β 2.2 m
7 5.54 m
9 5.54 m
10 5.54 m
14α 2.65 d 19.2
14β 2.98 dd 19.2, 12
16 1.21 s
17 3.69 d 8
17' 4.2 d 8
18 1.25 s
19 4.34 d 12.4
19' 4.44 d 12.4
20 4.59 s
20' 5.54 m
Ac 1.97 s
Ac 1.97 s
Ac 2.2 s
Ac 2.12 s
Ac 2.15 s
2' 6.8 d 16
3' 7.92 d 16
phenyl 7.57 m

Carbon NMR Peaks

Position PPM
1 48.7
2 70.5
3 39.9
4 140.8
5 73.8
6 37.1
7 69.2
8 49.1
9 68.4
10 65.3
11 82.3
12 91.7
13 204.4
14 32.3
15 49.7
16 15.1
17 80.4
18 12.2
19 61.6
20 115.4
Ac 20.9
Ac 20.6
Ac 21.3
Ac 20.9
Ac 21.3
Ac 168.9
Ac 167
Ac 169.9
Ac 170.8
Ac 172.2
1' 166
2' 117.7
3' 146.3
i-phenyl 134.7
o-phenyl 128.8
m-phenyl 127.9
p-phenyl 130.2