Y. Zhu, J. Ralph / Tetrahedron Letters 52 (2011) 3729–3731
3731
Cl
O
Cl
O
O
O
O
Cl
O
OH
Cl
ClCH
2
COCl, Py, CH
C, 99%
2
Cl
2
N
2
H
4.CH
3
CO
2
H, DMF
3 2 2
CCl CN, DBU, CH Cl
O
O
O
HO
HO
O
O
O
o
o
0
O
Cl
0
C, 71%
O
87%
OH OH
O
O
O
OH
Cl
Cl
O
O
O
O
Cl
Cl
3
4
OCH
3
Cl
HO
O
Cl
Cl
O
O
O
O
R
OH
O
O
O
O
6 R = H
R = OCH
O
Cl
Cl
OCH
3
O
7
3
OCH
Py, H
2
O
HO
HO
O
3
O
NH
CCl
O
O
O
OH
O
TMSOTf, 4 A MS, CH
2
Cl
2
O
O
O
OH
O
O
O
3
O
R'
Cl
Cl
R
O
O
O
O
R
Cl
Cl
1 R = H, 80% from 8a
78% from 8b
2 R = OCH , 85% from 9a
0% from 9b
5
8
9
R = H, 72% (8a/8b = 1:1) from 6
a R' = COCH Cl 8b R' = H
R = OCH , 51% (9a/9b = 2:1) from 7
3
8
2
8
3
9
2
a R' = COCH Cl, 9b R' = H
Scheme 1. Synthesis of 1-O-b-feruloyl and 1-O-b-sinapoyl glucopyranoses.
Science BER DE-FC02-07ER64494), and the Department of Bio-
chemistry, University of Wisconsin-Madison for support of this
research.
4. (a) Liu, H.; Wang, X.; Zhang, H.; Yang, Y.; Ge, X.; Song, F. Gene 2008, 420, 57; (b)
Stehle, F.; Brandt, W.; Schmidt, J.; Milkowski, C.; Strack, D. Phytochemistry 2008,
6
9, 1826; (c) Mugford, S. T.; Qi, X.; Bakht, S.; Hill, L.; Wegel, E.; Hughes, R. K.;
Papadopoulou, K.; Melton, R.; Philo, M.; Sainsbury, F.; Lomonossoff, G. P.; Roy,
A. D.; Goss, R. J. M.; Osbourn, A. Plant Cell 2009, 21, 2473.
5
6
.
.
Obel, N.; Porchia, A. C.; Scheller, H. V. Planta 2003, 216, 620.
Supplementary data
(a) Ralph, J.; Grabber, J. H.; Hatfield, R. D. Carbohydr. Res. 1995, 275, 167; (b)
Ralph, J.; Hatfield, R. D.; Grabber, J. H.; Jung, H.-J. G.; Quideau, S.; Helm, R. F. ACS
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Supplementary data (experimental procedures and H and 13C
NMR spectra for the complete synthesis of compounds 1 and 2)
1
7
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1
1, 278; (b) Simmons, B. A.; Loque, D.; Ralph, J. Curr. Opin. Plant Biol. 2010, 13,
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1
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1
2
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2
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