2α,9α,10β-triacetoxytaxa-4(20),11-dien-13-one-5α-O-β-D-glucopyranoside

2α,9α,10β-triacetoxytaxa-4(20),11-dien-13-one-5α-O-β-D-glucopyranoside

Common Name: 2α,9α,10β-triacetoxytaxa-4(20),11-dien-13-one-5α-O-β-D-glucopyranoside

Synonyms: 2α,9α,10β-triacetoxy-5α-(β-D-glucopyranoside)taxa-4(20),11-dien-13-one

CAS Registry Number: 857419-44-4

InChI: InChI=1S/C32H46O13/c1-13-19(37)11-18-27(41-15(3)34)23-14(2)20(44-30-26(40)25(39)24(38)21(12-33)45-30)9-10-32(23,8)29(43-17(5)36)28(42-16(4)35)22(13)31(18,6)7/h18,20-21,23-30,33,38-40H,2,9-12H2,1,3-8H3/t18-,20-,21+,23-,24+,25-,26+,27+,28+,29-,30+,32+/m0/s1

InChIKey: InChIKey=OUZIYNFFWIKDCK-MSFHKKQRSA-N

Formula: C32H46O13

Molecular Weight: 638.7

Exact Mass: 638.2938

NMR Solvent: acetone-d6

MHz: 500.0

Calibration: Solvent signals 2.02 ppm for proton and 29.9 for cabon.

NMR references: Li, L., Cao, C., Huo, C., Zhang, M., Shi, Q., and Kiyota, H. (2005). Structure elucidation and complete NMR spectral assignments of a new taxane glycoside from the needles of Taxus cuspidata. Magnetic Resonance in Chemistry 43, 475–478.

Species: Taxus

Notes: Coupling constant for 6'-OH not reported due to overlap.

Proton NMR Peaks

Position PPM Peak Type J (Hz)
1 2.23 m
2 5.57 dd 6.2, 1.8
3 3.33 d 6.2
5 4.09 t 2.7
6a 2.07 m
6b 1.56 m
7a 1.78 m
7b 1.66 m
9 5.89 d 10.5
10 6.01 d 10.5
14a 2.78 dd 19.8, 7.1
14b 2.47 d 19.8
16 1.11 s
17 1.72 s
18 2.22 s
19 0.88 s
20a 5.18 br s
20b 4.82 t 1.3
2-OAc 2.04 s
9-OAc 2.07 s
10-OAc 2.04 s
1' 4.27 d 7.9
2' 3.16 m
2'-OH 3.49 d 4.8
3' 3.32 m
4' 3.32 m
5' 3.26 m
6'a 3.82 m
6'b 3.62 m
6'-OH 3.47 t

Carbon NMR Peaks

Position PPM
1 48.5
2 69.2
3 42.3
4 145.1
5 85
6 29.9
7 27.3
8 44.1
9 75.3
10 72.9
11 150.7
12 138
13 201.2
14 36.1
15 37.4
16 36.6
17 24.5
18 13.5
19 17
20 114.3
2-OAc 20
2-OAc 168.9
9-OAc 19.5
9-OAc 169.6
10-OAc 20
10-OAc 169.4
1' 103.6
2' 73.6
3' 77.1
4' 70.6
5' 76.4
6' 62