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2
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0141741232
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-
For recent works describing transition-metal-mediated cleavage with Os reagent, see: a
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For recent works describing transition-metal-mediated cleavage with Os reagent, see: (a) Ley, S. V.; Ramarao, C.; Lee, A.; Ostergaard, N.; Smith, S. C.; Shirley, I. M. Org. Lett. 2003, 5, 185.
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Ley, S.V.1
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Ostergaard, N.4
Smith, S.C.5
Shirley, I.M.6
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3
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0037123252
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(b) Travis, B. R.; Narayan, R. S.; Borhan, B. J. Am. Chem. Soc. 2002, 124, 3824.
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J. Am. Chem. Soc
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Travis, B.R.1
Narayan, R.S.2
Borhan, B.3
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4
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33644784644
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With AuCl reagent, see: Xing, D, Guan, B, Cai, G, Fang, Z, Yang, L, Shi, Z. Org. Lett. 2006, 8, 693
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(c) With AuCl reagent, see: Xing, D.; Guan, B.; Cai, G.; Fang, Z.; Yang, L.; Shi, Z. Org. Lett. 2006, 8, 693.
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5
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17844369291
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Murahashi, S, Ed, Wiley-VCH: Weinheim
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Murahashi, S.; Komiya, N. In Ruthenium in Organic Synthesis; Murahashi, S., Ed.; Wiley-VCH: Weinheim, 2004, 65-69.
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Murahashi, S.1
Komiya, N.2
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6
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33745583791
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For recent typical examples, see: a
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For recent typical examples, see: (a) Kim, W.; Park, I.; Park, J. Org. Lett. 2006, 8, 2543.
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Org. Lett
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Kim, W.1
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7
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0037467025
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(b) Zhan, B.; White, M. A.; Sham, T.; Pincock, J. A.; Doucet, R.; Rao, K. V. R.; Robertson, K. N.; Cameron, T. S. J. Am. Chem. Soc. 2003, 125, 2195.
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Zhan, B.1
White, M.A.2
Sham, T.3
Pincock, J.A.4
Doucet, R.5
Rao, K.V.R.6
Robertson, K.N.7
Cameron, T.S.8
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8
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0036827711
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(c) Cheung, W.; Yu, W.; Yip, W.; Zhu, N.; Che, C. J. Org. Chem. 2002, 67, 7716.
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J. Org. Chem
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Cheung, W.1
Yu, W.2
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Zhu, N.4
Che, C.5
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9
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0034718073
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and references cited therein
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(d) Yamaguchi, K.; Mori, K.; Mizugaki, T.; Ebitani, K.; Kaneda, K. J. Am. Chem. Soc. 2000, 122, 7144; and references cited therein.
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Yamaguchi, K.1
Mori, K.2
Mizugaki, T.3
Ebitani, K.4
Kaneda, K.5
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10
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4644293702
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For an excellent work detailing control of the oxidation stage with immobilized Ru species, see
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For an excellent work detailing control of the oxidation stage with immobilized Ru species, see: Ho, C.; Yu, W.; Che, C. Angew. Chem. Int. Ed. 2004, 43, 3303.
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Angew. Chem. Int. Ed
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Ho, C.1
Yu, W.2
Che, C.3
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12
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7044237373
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(b) Fukusaki, F.; Takeno, S.; Takeshi Bamba, T.; Okumoto, H.; Katto, H.; Kajiyama, S.; Kobayashi, A. Biosci., Biotechnol., Biochem. 2004, 68, 1988.
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Biosci., Biotechnol., Biochem
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Fukusaki, F.1
Takeno, S.2
Takeshi Bamba, T.3
Okumoto, H.4
Katto, H.5
Kajiyama, S.6
Kobayashi, A.7
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13
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Tada, M.; Yamashita, Y.; Petrykin, V.; Osada, M.; Yoshida, K.; Kakihana, M. Chem. Mater. 2002, 14, 2845.
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Tada, M.1
Yamashita, Y.2
Petrykin, V.3
Osada, M.4
Yoshida, K.5
Kakihana, M.6
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14
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2542433188
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Carlsen, P. H. J.; Katsuki, T.; Martin, V. S.; Sharpless, K. B. J. Org. Chem. 1981, 46, 3936.
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Carlsen, P.H.J.1
Katsuki, T.2
Martin, V.S.3
Sharpless, K.B.4
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15
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0035854317
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3 leading to aldehyde, see: (a) Yang, D.; Zhang, C. J. Org. Chem. 2001, 66, 4814.
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3 leading to aldehyde, see: (a) Yang, D.; Zhang, C. J. Org. Chem. 2001, 66, 4814.
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16
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33645501568
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3 leading to diol, see: (b) Tiwari, P.; Misra, A. K. J. Org. Chem. 2006, 71, 2911.
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3 leading to diol, see: (b) Tiwari, P.; Misra, A. K. J. Org. Chem. 2006, 71, 2911.
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19
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9344260283
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3 leading to acyloin, see: Plietker, B. J. Org. Chem. 2004, 69, 8287.
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3 leading to acyloin, see: Plietker, B. J. Org. Chem. 2004, 69, 8287.
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20
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33846649589
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The sugar derivatives 8, 11 and 13 were prepared from D-ribose, D-arabinose and D-xylose, respectively, according to the literature, followed by usual acetylation: (a) Shing, T. K. M.; Wong, W. F.; Ikeno, T.; Yamada, T. Org. Lett. 2007, 9, 207.
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The sugar derivatives 8, 11 and 13 were prepared from D-ribose, D-arabinose and D-xylose, respectively, according to the literature, followed by usual acetylation: (a) Shing, T. K. M.; Wong, W. F.; Ikeno, T.; Yamada, T. Org. Lett. 2007, 9, 207.
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23
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37749041099
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The acetate 15 was synthesized by reaction of the aldehyde 19 and allyl Grignard reagent, followed by acetylation as illustrated in (Chemical Equation Presented) Scheme 4. For preparation of the intermediate aldehyde 19, see ref. 10a and: Calinaud, P.; Gelas, J. In Preparative Carbohydrate Chemistry; Hanessian, S., Ed.; Marcel Dekker: New York, 1996, p15.
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(d) The acetate 15 was synthesized by reaction of the aldehyde 19 and allyl Grignard reagent, followed by acetylation as illustrated in (Chemical Equation Presented) Scheme 4. For preparation of the intermediate aldehyde 19, see ref. 10a and: Calinaud, P.; Gelas, J. In Preparative Carbohydrate Chemistry; Hanessian, S., Ed.; Marcel Dekker: New York, 1996, p15.
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-
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24
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33947185293
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The diacetonide 17 is readily accessible from D-mannose: Shing, T. K. M.; Wong, W. F.; Cheng, H. M.; Kwok, W. S.; So, K. H. Org. Lett. 2007, 9, 753.
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(e) The diacetonide 17 is readily accessible from D-mannose: Shing, T. K. M.; Wong, W. F.; Cheng, H. M.; Kwok, W. S.; So, K. H. Org. Lett. 2007, 9, 753.
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25
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37749021914
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2O. Filtrates were extracted with EtOAc and the organic layer was dried and concentrated. The residue was then chromatographed on silica gel to give the product.
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2O. Filtrates were extracted with EtOAc and the organic layer was dried and concentrated. The residue was then chromatographed on silica gel to give the product.
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26
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37749018447
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2a: 1H NMR (300 MHz, CDCl3, δ, 0.85 (t, J, 7.6 Hz, 3 H, 1.25 (t, J, 7.2 Hz, 6 H, 2.05 (q, J, 7.6 Hz, 2 H, 2.17 (s, 3 H, 3.10 (s, 2 H, 4.19 (q, J, 7.0 Hz, 4 H, 13C NMR (75 MHz, CDCl3, δ, 8.8, 13.7, 26.2, 30.0, 45.2, 55.6, 61.1, 170.5, 204.9. 2b: a mixture of separable diastereomers in a ratio of ca. 4:1. Major product: 1H NMR (500 MHz, CDCl 3, δ, 1.04 (d, J, 6.4 Hz, 3 H, 1.43 (ddd, J, 3.3, 13.1, 26.3 Hz, 1 H, 1.73 (ddd, J, 3.4, 13.1, 25.6 Hz, 1 H, 2.19 (s, 3 H, 2.08-2.25 (m, 2 H, 2.35-2.45 (m, 1 H, 2.45-2.52 (m, 2 H, 2.77-2.86 (m, 1 H, 13C NMR (126 MHz, CDCl3, δ, 14.2, 27.7, 28.2, 34.5, 42.6, 44.5, 52.1, 208.1, 211.4. Minor product: 1H NMR (500 MHz, CDCl3, δ, 1.09 (d, J, 7.0 Hz, 3 H, 1.50-1.58 (m, 1 H, 1.91-2.10 (m, 3 H, 2.18 s, 3 H, 2.30-2.42
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3): δ = 1.27
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