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and references therein
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33845470339
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Pyrromycinone, 9, was obtained by acidic hydrolysis of marcellomycin, a generous gift from Bristol-Myers Squibb. Pyrromycinone can also be obtained through known synthetic routes or through degradation of other readily available anthracyclines; see: (a) Hauser, F. M.; Mal, D. J. Am. Chem. Soc. 1984, 706, 1098.
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27
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33646951503
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There may be more than one highly reactive sulfenylating agent produced in the reaction
-
There may be more than one highly reactive sulfenylating agent produced in the reaction.
-
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33
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37049103342
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35
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33646955207
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note
-
This specific alkene was chosen for a number of reasons: it is commercially available and inexpensive, and has a sufficiently high boiling point to permit azeotroping with toluene along with the other starting materials prior to reaction.
-
-
-
-
36
-
-
33646958906
-
-
note
-
Norbornylene was slightly less effective than 4-allyl-1,2-dimethoxybenzene, while vinylnorbornene, vinylnaphthalene, cyclopentene, and vinyltrimethylsilane were significantly less effective. No product was formed in the presence of triphenylphosphine or thioanisole.
-
-
-
-
37
-
-
33646952515
-
-
note
-
For comparison, glycosylation of 15 with sulfoxide 11 in the absence of a scavenger produced 16 in 45% yield along with 18% of the corresponding trisaccharide, showing that most of the improvement in yield is a result of the scavenger. However, similar improvements in yield (ID-15%) are observed when the C ring sulfoxide is coupled. These modest improvements in yield achieved by incorporating the 2,6-dichlorophenyl sulfide become important when multiple glycosylations are conducted.
-
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38
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33845281396
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39
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33646960951
-
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For example, sulfenylating agents are known to react with alcohols, amines, and electron-rich aromatic rings. See ref 22
-
For example, sulfenylating agents are known to react with alcohols, amines, and electron-rich aromatic rings. See ref 22.
-
-
-
-
40
-
-
44949268152
-
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In addition to activating glycosyl sulfides, sulfenylating agents have been used to activate glycosyl xanthates and glycals. For activation of xanthates, see: (a) Marra, A.; Sinay, P. Carbohydr. Res. 1990, 195, 303.
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47
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33646957342
-
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The known C ring sulfoxide 6 can be synthesized from rhamnose in seven steps (58% overall yield); see ref 7
-
The known C ring sulfoxide 6 can be synthesized from rhamnose in seven steps (58% overall yield); see ref 7.
-
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48
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84985666791
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Adam, W.; Bialas, J.; Hadjiarapoglou, L. Chem. Ber. 1991, 124, 2377.
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49
-
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33646957416
-
-
13C, and mass spectra for synthetic ciclamycin 0 were identical with the spectra reported in the literature (see refs 6 and 8)
-
13C, and mass spectra for synthetic ciclamycin 0 were identical with the spectra reported in the literature (see refs 6 and 8).
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-
-
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