Carbohydrate Chemistry Volume 10 by J S Brimacombe

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By J S Brimacombe

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2-Esters (60) could also be prepared in high yield by reaction of methyl a-D-glucopyranoside with an equimolar proportion of dibutyltin oxide in methanol, to yield the 2,3-O-dibutylstannylene derivative (59), and then with an acid chloride in the presence of triethylamine (Scheme 19). Other examples of / OH OH / BU, (59) Reagents: i, Bu,SnO-MeOH; ii, RCOCl-Et3N Scheme 19 19* R. M. Munavu and H. H. Szmant, J. Org. , 1976,41, 1832. 202 Similarly, the 0 II RCH,OCK R C H, OSn Bu (63) “CMe, Reagents: i, NBS-CCl,; ii, PhCHO-NBS-CCI, Scheme 20 reaction of 1,2:5,6-di-O-isopropylidene-3-O-tributylstannyl-~-~-glucofuranose with NBS and n-hexanal furnished the corresponding 3-hexanoate in high yield.

Akad. , Ser. , 1975, 1843 (Chem. , 1976, 84, 31 3192). L. L. Danilov, L. V. Volkova, and R. P. Evstigneeva, Zhur. ,1975, 45, 2307 (Chem. , 1976, 84, 105 919n). L. L. Danilov, L. V. Volkova, V. A. Bondarenko, and R. P. Evstigneeva, Bioorg. , 1975, 1, 905 (Chem. , 1976, 84, 105 921p). M. A. Grum-Grzhimailo, L. V. Volkova, and R. P. Evstigneeva, Zhur. , 1976, 46, 1386 (Chem. A h , 1976, 85, 143 372p). P. F. Blackmore, J. F. Williams, and J . K. S. Letters, 1976, 64, 222. N. K. Kochetkov, E. E. Nifant’ev, M.

E. Pfeffer, E. S. Rothman, and G. G. Moore, J. Org. , 1976, 41, 2925. T. D. Audichya, IndinnJ. , 1976, 14B, 111 (Chem. , 1976, 85, 177 809b). S. Ando, T. Ariga, and T. Yamakawa, Bull. Chem. Japan, 1976, 49, 1335. J. G. Buchanan and A. R. , 1976, 49, 289. H. Paulsen, H. Hohne, and P. L. Durette, Chem. , 1976, 109, 597. H. Paulsen and R. Dammeyer, Chem. , 1976, 109, 1837. ~~ The conversion of adenosine into a 2’,3’-O-alkoxymethylene derivative is noted in Chapter 21,224and the formation of the thio-orthoester (24) from methyl (1 ,2,3,4-tetra- O-acetyl- a - ~ - gucopyranosy1)uronate l is mentioned in Chapter 3.

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