10-​Acetylglycolylbaccat​in IV

10-​Acetylglycolylbaccat​in IV

Common Name: 10-​Acetylglycolylbaccat​in IV

Synonyms: (10β-O-acetylglycolyl)baccatin VI

CAS Registry Number: 340739-94-8

InChI: InChI=1S/C39H48O16/c1-19-26(50-21(3)41)16-39(47)34(54-35(46)25-13-11-10-12-14-25)32-37(9,27(51-22(4)42)15-28-38(32,18-49-28)55-24(6)44)33(52-23(5)43)31(30(19)36(39,7)8)53-29(45)17-48-20(2)40/h10-14,26-28,31-34,47H,15-18H2,1-9H3/t26-,27-,28+,31+,32-,33-,34-,37+,38-,39+/m0/s1

InChIKey: InChIKey=PZULTXJQGXGNMM-UKKCMPINSA-N

Formula: C39H48O16

Molecular Weight: 772.79

Exact Mass: 772.2942

NMR Solvent: CDCl3

MHz:

Calibration:

NMR references: Zhang, J., Sauriol, F., Mamer, O., You, X.-L., Alaoui-Jamali, M.A., Batist, G., and Zamir, L.O. (2001). New Taxane Analogues from the Needles of Taxus canadensis. J. Nat. Prod. 64, 450–455.

Species: Taxus

Notes:

Proton NMR Peaks

Position PPM Peak Type J (Hz)
2 5.85 d 6
3 3.15 d 6
5 4.95 d 8.8
6a 2.48 dt 15, 8.2
6b 1.87 ddd 15, 10, 1.2
7 5.53 dd 9.1, 8
9 6.02 d 11.5
10 6.31 d 11.5
13 6.16 t 8.9
14 2.2 m
16 1.23 s
17 1.75 s
18 2.04 d 1
19 1.59 s
20a 4.32 d 8.3
20b 4.11 d 8.3
OAc 2.28 s
OAc 2.18 s
OAc 2.15 s
OAc 2.14 s
OAc 2.09 s
Ph-o 8.08 d 7.3
Ph-m 7.47 t 7.3
Ph-p 7.6 t 7
CH2 2' 4.57 d 16
CH2 2' 4.47 d 16

Carbon NMR Peaks

Position PPM
1 78.9
2 73.1
3 47.2
4 81.6
5 83.7
6 34.3
7 71.5
8 45.9
9 74.3
10 71.5
11 133.2
12 142.2
13 69.5
14 35
15 42.8
16 28.1
17 22.1
18 14.8
19 12.5
20 76.3
OAc 22.6
OAc 169
OAc 20.9
OAc 170.3
OAc 20.3
OAc 170.2
OAc 21.1
OAc 170
OAc 20.7
OAc 168.9
OBz C=O 166.7
Ph-o 129.9
Ph-m 128.5
Ph-p 133.5
C=O 1' 165.9
1' 170
2' 60.2