Advances in Carbohydrate Chemistry and Biochemistry Volume 39 This Page Intentionally Left Blank Advances in Carbohydrate Chemistry and Biochemistry Editors R. STUART TIPSON DEREK HORTON Board of Advisors BENGT LINDBERG HANSPAULSEN NATHAN SHARON MAURICE STACEY ROY L. WHISTLER LAURENSANDERSON STEPHEN J. ANGYAL GUY G. S. DUTTON ALLAN B. FOSTER DEXTERFRENCH Volume 39 1981 ACADEMIC PRESS A Subsidiary of Harcourt Brace Jovanovich, Publishers New York London Toronto Sydney San Francisco COPYRIGHT @ 1981, B Y ACADEMIC PRESS,INC. ALL RIGHTS RESERVED. NO PART O F THIS PUBLICATION MAY BE REPRODUCED OR TRANSMITTED IN ANY FORM OR BY ANY MEANS, ELECTRONIC OR MECHANICAL, INCLUDING PHOTOCOPY, RECORDING, OR ANY INFORMATION STORAGE AND RETRIEVAL SYSTEM, WITHOUT PERMISSION IN WRITING FROM T H E PUBLISHER. ACADEMIC PRESS, INC. 111 Fifth Avenue, New York, New York 10003 United Kingdom Editiori published by ACADEMIC PRESS, INC. ( L O N D O N ) LTD. 24/28 Oval Road, London N W l IDX LIBRARY OF CONGRESS CATALOG CARDNUMBER:45-11351 ISBN 0-1 2-007239-4 PRINTED IN TH E UNITED STATES O F AMERICA 81 82 83 84 9 8 7 6 5 4 3 2 1 CONTENTS LISTOF CONTRIBUTORS . . . . . . . . . . . . . . . . . . . . . . . . . . . PREFACE. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . vii ix Karl Paul Gerhardt Link (1901-1978) CLINTONE . BALLOU Text . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1 The Selective Removal of Protecting Groups in Carhohydrate Chemistry ALAN H . HAINES I . Introduction . . . . . . . . . . I1. Deacetalation . . . . . . . . . I11. Deacylation . . . . . . . . . . IV. Dealkylation . . . . . . . . . . V. Deborination and Deboronation . VI . Denitration . . . . . . . . . . VII . Dephosphonylation. . . . . . . VIII . De(trialkylsi1y)ation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 13 14 28 44 53 55 58 62 The Reactivity of Cyclic Acetals of Aldoses and Aldosides JACQUES I. I1. I11. IV . GELAS Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 71 Summary of Developments Concerning the Synthesis of Cyclic Acetals . . 73 Reactivity . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 81 Conclusion . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 155 Synthesis and Polymerization of Anhydro Sugars CONRADSCHUERCH I . Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . I1. Synthesis of Anhydro-aldoses and -ketoses . . . . . . . . . . . . . . I11. Polymerization of Anhydroaldoses . . . . . . . . . . . . . . . . . . IV. Summary and Prospects . . . . . . . . . . . . . . . . . . . . . . . . 157 . 160 . 173 211 The Chemistry of Maltose RIAZ KHAN I . Introduction . . . . . I1. Structure and Synthesis . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . V 214 214 CONTENTS vi I11 . Glycosides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . IV . Ethers . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 217 219 V . Esters . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 223 VI . Nucleophilic-displacement Reactio