10-​(Hydroxyacetyl)​baccatin VI

10-​(Hydroxyacetyl)​baccatin VI

Common Name: 10-​(Hydroxyacetyl)​baccatin VI

Synonyms: 6-​Deacetyl-​6-​(hydroxyacetyl)​baccatin VI

CAS Registry Number: 166662-47-1

InChI: InChI=1S/C37H46O15/c1-18-24(47-19(2)39)15-37(45)32(51-33(44)23-12-10-9-11-13-23)30-35(8,25(48-20(3)40)14-26-36(30,17-46-26)52-22(5)42)31(49-21(4)41)29(50-27(43)16-38)28(18)34(37,6)7/h9-13,24-26,29-32,38,45H,14-17H2,1-8H3/t24-,25-,26+,29+,30-,31-,32-,35+,36-,37+/m0/s1

InChIKey: InChIKey=IOLUMVDSGVZBKU-RXLGKBJNSA-N

Formula: C37H46O15

Molecular Weight: 730.75

Exact Mass: 730.2837

NMR Solvent: CDCl3

MHz: 500.0

Calibration: Residual solvent 7.25 ppm and 77.0 ppm for proton and carbon respectively.

NMR references: Zamir, L.O., Nedea, M.E., Zhou, Z.-H., Bélair, S., Caron, G., Sauriol, F., Jacqmain, E., Jean, F.I., Garneau, F.-X., and Mamer, O. (1995). Taxus canadensis taxanes: structures and stereochemistry. Canadian Journal of Chemistry 73, 655–665.

Species: Taxus

Notes: Coupling constants not reported for protons at positions 3, 18, and protons on aromatic ring.

Proton NMR Peaks

Position PPM Peak Type J (Hz)
2 5.87 d 5.9
3 3.16 d
5 4.96 d 9.3
6A 2.49 dt 15.1, 8.3
6B 1.89 m
7 5.56 dd 9.3, 7.8
9 6.03 d 11.3
10 6.4 d 11.3
13 6.18 br t 8.3
14A 2.22 m
14B 2.19 m
16 1.22 s
17 1.74 s
18 2.07 d
19 1.6 s
20A 4.33 d 8.3
20B 4.12 d 8.3
11'-A 4.09 d 16.6
11'-B 4.03 d 16.6
Ac 2.29 s
Ac 2.2 s
Ac 2.11 s
Ac 2.1 s
benzoyl ortho 8.09 d
benzoyl meta 7.48 t
benzoyl para 7.61 t

Carbon NMR Peaks

Position PPM
1 79.2
2 73
3 47.1
4 81.8
5 83.5
6 34.2
7 71.6
8 46.1
9 74.5
10 71.9
11 133.6
12 142.8
13 69.5
14 34.8
15 42.8
16 28.1
17 22
18 14.7
19 12.4
20 76.3
Ac 22.6
Ac 169.7
Ac 20.8
Ac 170.8
Ac 21.1
Ac 170.4
Ac 20.5
Ac 170.8
Benzoyl (CO) 167.5
Benzoyl C-1 128.8
Benzoyl C-2, 6 130.2
Benzoyl C-3, 5 128.8
Benzoyl C-4 133.7
10' 172.3
11' 60.5