Integrated route to the L-aldohexoses using a common man-made chiral building block.

作者: Miwako Takeuchi , Takahiko Taniguchi , Kunio Ogasawara

DOI: 10.1002/(SICI)1520-636X(2000)12:5/6<338::AID-CHIR6>3.0.CO;2-Y

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摘要: Starting from a common man-made chiral sugar building block, five out of eight L-aldohexoses have been synthesized in diastereocontrolled manner to complete an integrated synthesis the possible aldohexoses; remaining three L-hexoses were same block. Thus, L-altrose, L-mannose, L-allose, L-talose, and L-glucose obtained present investigation on basis inherent convex-face selectivity exerted by Chirality 12:338–341, 2000. © 2000 Wiley-Liss, Inc.

参考文章(13)
S. Y. KO, A. W. M. LEE, S. MASAMUNE, L. A. REED, K. B. SHARPLESS, F. J. WALKER, Total synthesis of the L-hexoses. Science. ,vol. 220, pp. 949- 951 ,(1983) , 10.1126/SCIENCE.220.4600.949
Steven V. Ley, Joanne Norman, William P. Griffith, Stephen P. Marsden, Tetrapropylammonium Perruthenate, Pr4N+RuO4-, TPAP: A Catalytic Oxidant for Organic Synthesis Synthesis. ,vol. 1994, pp. 639- 666 ,(1994) , 10.1055/S-1994-25538
Katsuya Matsumoto, Takashi Ebata, Koshi Koseki, Hiroshi Kawakami, Hajime Matsushita, Synthesis of D-Allosan from Levoglucosenone Heterocycles. ,vol. 32, pp. 2225- ,(1991) , 10.3987/COM-91-5872
M. Prystaš, H. Gustafsson, F. Šorm, The epoxide ring opening of 2-O-acyl-1,6:3,4-dianhydro-β-D-galactopyranoses Collection of Czechoslovak Chemical Communications. ,vol. 36, pp. 1487- 1495 ,(1971) , 10.1135/CCCC19711487
Matthew J. Gaunt, Jinquan Yu, Jonathan B. Spencer, Rational Design of Benzyl-Type Protecting Groups Allows Sequential Deprotection of Hydroxyl Groups by Catalytic Hydrogenolysis Journal of Organic Chemistry. ,vol. 63, pp. 4172- 4173 ,(1998) , 10.1021/JO980823V
James G. Smith, Peter W. Dibble, Richard E. Sandborn, The preparation and reactions of naphtho[1,2-c]furan and naphtho[2,3-c]furan Journal of Organic Chemistry. ,vol. 51, pp. 3762- 3768 ,(1986) , 10.1021/JO00370A004
Solomon Marmor, The Epoxidation of Certain α,β-Unsaturated Ketones with Sodium Hypochlorite Journal of Organic Chemistry. ,vol. 28, pp. 250- 251 ,(1963) , 10.1021/JO01036A526