Carbohydrate Chemistry Volume 4 by John Stuart Brimacombe

By John Stuart Brimacombe

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98). Application of the Corey and Winter procedure to the thionocarbonate (84) had previously been shown to yield the 5,6-olefin in high yield. The s=c orthoester (85) has now been recognised as a by-product, and it was concluded that the elimination probably proceeds by way of the carbene (86). 78 17' 178 D. Trimnell, W. M. Doane, C . R. Russell, and C . E. , 1970, 13, 301. D. Horton and C. G . Tindall, J. Org. , 1970, 35, 3558. -Full details of the synthesis of monophosphate esters from alcohols and o-phenylene phosphorochloridate (87) (Scheme 20) Reagents: i, ROX, excess base; ii, Br,-aq.

Ogawa, T. Shoji, and N. Kato, Bull. Chem. SOC. Japan, 1970, 43, 1219. B. H. , 1970, 13, 193. K. Stellner, 0. Westphal, and H. Mayer, Annalen, 1970, 738, 179. A. B. Zanlungo, J. 0. Deferrari, and R. A. Cadenas, J. Chem. SOC. ( C ) , 1970, 1908. A. S. Cerezo, A. B. Zanlungo, J. 0. Deferrari, and R. A. Cadenas, Chem. , 1970, 1051. H. Paulsen, Chimia, 1970, 24, 290. H. -P. Herold, Chem. , 1970, 103, 2450. Esters 'c> 37 CH, Br Me +o-cH2 SbCf6 OAc I AcO Aco&oAc 1 I AcO (72) 1 (73) In a further paper,164related equilibria were reported.

Konowal, A . Zamojski, M. Masojidkova, and J. , 1970, 44, 1741. M. Cerny, T. Trnka, P. Beran, and J. Paciik, Coll. Czech. Chem. , 1969, 34, 3377. T. D. Inch and G . J. , 1970, 15, 1. -2,3-Di-O-acetyl- 1,6-anhydro-/3-~-glucopyranosehas been synthesised (Scheme 16) for use in Koenigs-Knorr preparations of 4-substituted D-glucose derivatives, since the reactivity of the 4-position of OAc OAc Reagents: i, H 3 0 + ;ii, Ac,O(l mol), py; iii, Me,C=CH,; iv, KOH; v, CF,CO,H Scheme 16 normal glucopyranoses in the C1 conformation is so low.

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