Carbohydrate Chemistry Volume 10 by J S Brimacombe PDF

By J S Brimacombe

ISBN-10: 0851860923

ISBN-13: 9780851860923

ISBN-10: 1847552870

ISBN-13: 9781847552877

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Extra resources for Carbohydrate Chemistry Volume 10

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Chem. , 1976, 832. A. Holy, J . Carbohydrates, Nucleosides, Nucleotides, 1975, 2, 25 1. 214 J. Stawinski, T. Hozumi, and S. A. S. Chem. , 1976, 243. g. 'l Metalation of 2,3,4,6-tetra-0-benzyl-~-g~ucopyranose using n-butyl-lithium in T H F at ca. 21s This sequence therefore provides a single pathway to 1-0-acyl-a- and -p-u-glucopyranoses. ~l~ The conversion of primary alcohols into chlorofluoroacetic esters is referred to in Chapter 7, while the formation of the unusual L-rhamnopyranosyl esters (22) and (23)124is dealt with in Chapter 3.

Tschesche and K. Struckmeyer, Chem. , 1976, 109, 2901. T. J. Cousineau and J. A. , J . Carbohydrates, Nucleosides, Nucleotides, 1976, 3, 146 J. M. J. Tronchet, B. Baehler, and A. Bonenfant, Helu. Chim. Acta, 1976, 59, 941. 140 141 142 143 185. g. g. methyl 4,6-O-benzylidene2,3- O-methylene- a-D-mannop yranoside). 146 A new cyclic ether, methyl 4,6- 0benzylidene-2,3- O-et hylene- a-~-gluco pyranoside, resulted when methyl 4,6-0benzylidene-a-D-glucopyranosidereacted with 1,2-dichloroethane under basic aqueous conditions in the presence of a phase-transfer catalyst.

173a T. Sassa and A. Takahama, Agric. and Biol. Chem. (Japan), 1975, 39, 2213. 174 0. , and B. , 1976, 50, 23. R Reagent: i, H,-Pd-C-THF = CHzOH or H (or EtOAc) Scheme 11 pyranose underwent rapid mutarotation when dissolved in water to give an equilibrium mixture containing mainly the a-pyranose (41%) and /3-furanose (42%) forms, together with the jS-pyranose and or-furanose forms (5 and 12%, not individually assigned). g. 177 Opening of the oxiran ring with ammonia provided a route to derivatives of methyl 4-acetamido-4,6-dideoxy-~-glucopyranoside, while the 4-azido-derivative (39), obtained with sodium azide, rapidly rearranged to give the 6-azido-derivative (40) (Scheme 13).

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Carbohydrate Chemistry Volume 10 by J S Brimacombe


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