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15
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84985205634
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11.
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-
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24
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84985284711
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15, and in the dissertation of, Techn. Hochschule Darmstadt
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(1980)
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Löhe, A.1
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29
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2742533527
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Large scale preparation of 8 from methyl α‐D‐glucopyranoside was conveniently effected by selective chlorination at C‐6, reductive dehalogenation and benzoylation, 193, followed by BHr treatment of the methyl 2,3,4‐tri‐O‐benzoly‐α‐D‐glucoside formed and ensuing dehydrobromination
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(1972)
Methods Carbohydr. Chem.
, vol.6
, pp. 177
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Evans, M.E.1
Parrish, F.W.2
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31
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84985177548
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21).
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-
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38
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84982073540
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Sugar enolones, XII. Peroxidation of pyranose-derived enol esters: An efficacious synthesis of peracetylhexosuloses and their conversion into γ-pyronesvia 3,2-enolones
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(1980)
Chemische Berichte
, vol.113
, pp. 489
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-
Lichtenthaler, F.W.1
Jarglis, P.2
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40
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84985203635
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27), in fact, has a negative long‐wave Cotton effect (Δε = −1.22 at 334 nm).
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-
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43
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84985203609
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15.
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44
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84985203620
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11, and literature given therein.
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46
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84985258977
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32
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47
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84985203631
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When the dimethoxyethane (DME) is thoroughly dry, e. g. by distillation from calcium hydride, the reduction of 13 proceeds sluggishly with the formation of several products other than 5; the same is observed with ether as solvent for reduction. Satisfactory results are obtained when using commercially available DME that has been partially dehydrated by absorptive filltration over alumina Woelm N, activ. I (50 g for 100 ml of DME, discarding the first 20 ml).
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-
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48
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84985203625
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15, p.
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-
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50
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84985205703
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-
3, instead of H), for wich a lengthy synthesis has recently been presented [, Abstract A 11, Chemiedozententagung Dortmund, March, ] allegedly has only an [α] D22 value of +71 in chloroform. Examination of the underlying preparative facts38, revealed though, that of the alltogether 13 steps required from D‐glucose, the last seven comprised sirupy products whose purification considerably impaired yields (7% for the concluding 4 steps) and that the target compound (4, R = CH3 instead of H) was obtained as a uniform oil, not not further purifiable by HPLC, and with analytical data which better fit a water addition product, conceivably a 2‐O‐methyl‐4,6‐dideoxy‐D‐hexos‐3‐ulose (ref.38), p. 56. Accordingly it may safely be concluded that for the methyl ether of 14, [Truncated]
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(1983)
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Kunz, H.1
Weißmüller, J.2
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