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Kojitriose: (a) Takeo, K. Carbohydr. Res. 1981, 88, 158-161. (b) Takeo, K.; Suzuki, Y. Carbohydr. Res. 1987, 162, 95-109. (c) Ref. 10g. (d) Reference 10h.
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25
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Kojitetraose and kojipentaose: (a) Reference 10g. (b) Reference 10h. (c) Reference 12b
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Kojitetraose and kojipentaose: (a) Reference 10g. (b) Reference 10h. (c) Reference 12b.
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12b used methyl 2-O-allyl-4,6-O- benzylidene-α-D-glucopyranoside as the precursor, which was prepared by several groups [(a) Küster, J. M.; Dyong, I. Liebigs Ann. Chem. 1975, 2179-2189. (b) Jenkins, D. J.; Potter, B. V. L. Carbohydr. Res. 1994, 265, 145-149. (c) Dasgupta, F.; Garegg, P. J. Synthesis 1994, 1121- 1123] by regioselective monoallylation of methyl 4,6-O-benzylidene- α-D-glucopyranoside. Careful reproduction of these protocols gave mixtures of the 2-O- and 3-O-allyl derivatives from which the isolation of the 2-O-allyl derivative proved to be impractical.
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0028761762
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12b used methyl 2-O-allyl-4,6-O- benzylidene-α-D-glucopyranoside as the precursor, which was prepared by several groups [(a) Küster, J. M.; Dyong, I. Liebigs Ann. Chem. 1975, 2179-2189. (b) Jenkins, D. J.; Potter, B. V. L. Carbohydr. Res. 1994, 265, 145-149. (c) Dasgupta, F.; Garegg, P. J. Synthesis 1994, 1121- 1123] by regioselective monoallylation of methyl 4,6-O-benzylidene- α-D-glucopyranoside. Careful reproduction of these protocols gave mixtures of the 2-O- and 3-O-allyl derivatives from which the isolation of the 2-O-allyl derivative proved to be impractical.
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12b used methyl 2-O-allyl-4,6-O- benzylidene-α-D-glucopyranoside as the precursor, which was prepared by several groups [(a) Küster, J. M.; Dyong, I. Liebigs Ann. Chem. 1975, 2179-2189. (b) Jenkins, D. J.; Potter, B. V. L. Carbohydr. Res. 1994, 265, 145-149. (c) Dasgupta, F.; Garegg, P. J. Synthesis 1994, 1121- 1123] by regioselective monoallylation of methyl 4,6-O-benzylidene- α-D-glucopyranoside. Careful reproduction of these protocols gave mixtures of the 2-O- and 3-O-allyl derivatives from which the isolation of the 2-O-allyl derivative proved to be impractical.
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Synthesis
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Garegg, P.J.2
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0027676464
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α,α-Dichloromethyl methyl ether (DCMME) has been used extensively for the introduction of chlorine to the anomeric center in methyl glycosides and glycosyl acetates, see, e.g.: Pozsgay, V.; Coxon, B.; Yeh, H. Bioorg. Med. Chem. 1993, 1, 237-257. For the only reported use of DCMME for the conversion of thioglycosides to glycosyl chlorides, see: Farkas, I.; Bognár, R.; Menyhárt, M. M.; Tarnai, A. K.; Bihari, M.; Tamás, J. Acta Chim. 1975, 84, 325-334.
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0010338213
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α,α-Dichloromethyl methyl ether (DCMME) has been used extensively for the introduction of chlorine to the anomeric center in methyl glycosides and glycosyl acetates, see, e.g.: Pozsgay, V.; Coxon, B.; Yeh, H. Bioorg. Med. Chem. 1993, 1, 237-257. For the only reported use of DCMME for the conversion of thioglycosides to glycosyl chlorides, see: Farkas, I.; Bognár, R.; Menyhárt, M. M.; Tarnai, A. K.; Bihari, M.; Tamás, J. Acta Chim. 1975, 84, 325-334.
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For an excellent review on the use of DCMME for the conversion of glycosyl acetates and O- and S-glycosides into glycosyl chlorides, see: Gross, H. Z. Chem. 1978, 18, 201-210.
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4 in ether to cleave the S-O linkage, see: Borén, H. B.; Ekborg, G.; Lönngren, J. Acta Chim. Scand. 1975, B29, 1085-1088.
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For related observations, see: (a) Szurmai, Z.; Lipták, A. Carbohydr. Res. 1982, 107, 33-41. (b) Szurmai, Z.; Lipták, A.; Schnatzke, G. Carbohydr. Res. 1990, 200, 201-208. (c) Borbás, A; Lipták, A. Carbohydr. Res. 1993, 241, 99-116.
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For related observations, see: (a) Szurmai, Z.; Lipták, A. Carbohydr. Res. 1982, 107, 33-41. (b) Szurmai, Z.; Lipták, A.; Schnatzke, G. Carbohydr. Res. 1990, 200, 201-208. (c) Borbás, A; Lipták, A. Carbohydr. Res. 1993, 241, 99-116.
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For related observations, see: (a) Szurmai, Z.; Lipták, A. Carbohydr. Res. 1982, 107, 33-41. (b) Szurmai, Z.; Lipták, A.; Schnatzke, G. Carbohydr. Res. 1990, 200, 201-208. (c) Borbás, A; Lipták, A. Carbohydr. Res. 1993, 241, 99-116.
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The synthesis of compound 30 from the same precursor in 42% yield was reported: Chénedé, A.; Perrin, E.; Rekaï, E. D.; Sinaÿ, P. Synlett 1994, 420-422.
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For an excellent review on the use of 2-(trimethylsilyl)ethyl glycosides in oligosaccharide synthesis, see: Magnusson, G. Trends Glycosci. Glycotechnol. 1992, 4, 358-367.
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