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12
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0344965444
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note
-
[6a] It has been reported
-
-
-
-
13
-
-
0344103051
-
-
note
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that ethyl 1-thiorhamnopyranosides are more reactive than the corresponding mannopyranosides.
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14
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33748601612
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[6b] N. L. Douglas, S. V. Ley, U. Lücking, S. L. Warriner, J. Chem. Soc., Perkin Trans. 1 1998, 51-66.
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16
-
-
0344534399
-
-
note
-
[17b] Prepared in the same way as 3a
-
-
-
-
17
-
-
0344103050
-
-
note
-
starting from 1,2,3,4-O-tetrabenzoyl-αβ-L-rhamnose.
-
-
-
-
18
-
-
0344534398
-
-
note
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2THF.
-
-
-
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19
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0025125757
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G. H. Veeneman, S. H. van Leeuwen, J. H. van Boom, Tetrahedron Lett. 1990, 31, 1331-1334.
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[10b] F. Andersson, P. Fügedi, P. J. Garegg, M. Nashed, Tetrahedron Lett. 1986, 27, 3919-3922.
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22
-
-
0344965441
-
-
note
-
The negative outcome of the glycosidation may be explained by the occurrence of a competing electrophilic aromatic substitution of the electron-rich phenyl ring in 12.
-
-
-
-
24
-
-
0344534395
-
-
note
-
[13a] Interestingly, no reaction of 6a with NIS in the presence of acetic acid [9] in dichloromethane was observed, indicating that 6a is more "disarmed" [13b] than a fully benzoylated ethyl 1-thiopyranosyl donor.
-
-
-
-
26
-
-
0344965439
-
-
note
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2) was accompanied by cleavage of the benzylidene acetal.
-
-
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27
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0025375498
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29
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0344534394
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-
note
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Monitoring the coupling reaction of 8a with 12 by TLC analysis revealed the presence of an intermediate, which was tentatively assigned as the corresponding orthoester.
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31
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0030998721
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To prevent migration of the caffeoyl ester function from HO-4 to HO-6 under mild basic conditions, the primary hydroxy group was protected with an acid-labile dimethoxytrityl (DMT) group see: S-Q. Zhang, Z-J. Li, A-B. Wang, M-S. Cai, R. Feng, Carbohvdr. Res. 1997, 299, 281-285.
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0001001018
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[26a] Cleavage of the phenolic silyl protecting groups with TBAF was reported to be troublesome; see: P. M. Kendall, J. V. Johnson, C. E. Cook, J. Org. Chem. 1979, 44, 1421-1424. See for alternative desilylation of phenolic tert-butyldimethylsilyl ethers:
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