Taxuspinanane A

Taxuspinanane A

Common Name: Taxuspinanane A

Synonyms:

CAS Registry Number: 187740-00-7

InChI: InChI=1S/C47H59NO14/c1-9-25(2)20-21-34(52)48-36(29-16-12-10-13-17-29)37(53)43(56)60-31-23-47(57)41(61-42(55)30-18-14-11-15-19-30)39-45(8,32(51)22-33-46(39,24-58-33)62-28(5)50)40(54)38(59-27(4)49)35(26(31)3)44(47,6)7/h10-19,25,31-33,36-39,41,51,53,57H,9,20-24H2,1-8H3,(H,48,52)/t25?,31-,32-,33+,36-,37+,38+,39-,41-,45+,46-,47+/m0/s1

InChIKey: InChIKey=LNTOLDCVMUNKRU-GVZBEMDZSA-N

Formula: C47H59N1O14

Molecular Weight: 861.97

Exact Mass: 861.3936

NMR Solvent: benzene-d6

MHz: 400.0

Calibration: Not mentioned in reference.

NMR references: Morita, H., Gonda, A., Wei, L., Yamamura, Y., Takeya, K., and Itokawa, H. (1997). Taxuspinananes A and B, New Taxoids from Taxus cuspidata var. nana. J. Nat. Prod. 60, 390–392.

Species: Taxus

Notes: Coupling constants not reported for br dd at positions 13 and 2' as well as 2'-OH. Two coupling constants were reported for doublet at 8.33 ppm which may be incorrect, therefore we left out these coupling constants from our table.

Proton NMR Peaks

Position PPM Peak Type J (Hz)
2 5.95 d 7
3 4.02 d 7
5 4.89 dd 9.5, 1.8
6α 2.58 m
6β 2.11 m
7 4.68 m
10 6.61 s
13 6.51 br dd
14 2.58 m
16 1.15 s
17 1.2 s
18 1.97 s
19 1.98 s
20a 4.35 d 8.6
20b 4.36 d 8.6
2' 4.63 br dd
3' 5.82 dd 9.2, 2
4' 6.09 d 9.2
6' 1.82 m
7' 1.27 m
7' 1.55 m
8' 1.14 m
9' 0.95 m
9' 1.12 m
10' 0.75 t 7.1
11' 0.7 d 6.4
1-OH 2.04 s
7-OH 2.97 d 4.2
2'-OH 3.76 br d
4-OAc 2.18 s
10-OAc 1.8 s
2-OBz 8.33 d
2-OBz 7.22 m
2-OBz 7.18 m
3'-Ph 7.39 d 7.3
3'-Ph 7.16 m
3'-Ph 7.11 m

Carbon NMR Peaks

Position PPM
1 79.45
2 75.69
3 46.26
4 81.64
5 84.55
6 36.19
7 72.71
8 59.15
9 203.52
10 76.03
11 133.96
12 142.23
13 72.71
14 36.33
15 43.68
16 22.11
17 26.92
18 14.82
19 10.07
20 76.54
1' 173.63
2' 73.11
3' 54.51
5' 172.99
6' 34.1
7' 32.51
8' 34.1
9' 29.46
10' 11.38
11' 18.84
4-OAc 22.55
4-OAc 170.46
10-OAc 20.42
10-OAc 171.23
2-OBz 130.68
2-OBz 128.89
2-OBz 133.42
2-OBz 130.35
2-OBz 167.13
3'-Ph 127.6
3'-Ph 128.98
3'-Ph 128.15
3'-Ph 139.31