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Allopyranosyl fluoride

The intermediate VII formed from the starting compound and diethyl-aminosulfur trifluoride reacts by an SN2 mechanism to yield a product with inversion of configuration on carbons 1 and 2, 2-benzyl-3-azido-4,6-0-benzylidene-3-deoxy- 3-D-allopyranosyl fluoride (IV) [8]. [Pg.45]

Good -selectivity (a as high as 1 16) was found on reaction of 4-Q-acetyl-6-deoxy-2,3-di-Q-methyl-/9-D-allopyranosyl fluoride (D-mycinosyl fluoride) with alcohols in the presence of silver perchlorate and bis(cyclopentadienyl)zirconium dichloride in benzene,and in related fashion a desosamine fluoride has been used to produce -glycosides under mild conditions involving a hafnium complex and the methods have been combined in a total synthesis of the macrocyclic glycoside mycinamycin IV. [Pg.16]

See other pages where Allopyranosyl fluoride is mentioned: [Pg.107]    [Pg.145]    [Pg.82]    [Pg.18]    [Pg.995]    [Pg.1106]    [Pg.1106]    [Pg.1160]    [Pg.1161]    [Pg.1161]    [Pg.107]    [Pg.145]    [Pg.82]    [Pg.18]    [Pg.995]    [Pg.1106]    [Pg.1106]    [Pg.1160]    [Pg.1161]    [Pg.1161]    [Pg.140]   


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