Allofuranoside

An alternative route to a furanosyl halide of 2-deoxy-D-nbo-hexose was envisaged, involving the lithium aluminum hydride reduction of ethyl 2,3-anhydro-/ -D-allofuranoside which could, presumably, lead to ethyl... 

In a number of reactions on furanose derivatives, steric restraints interfere with anhydro-ring formation. 6-Deoxy-2,3-0-isopropylidene-5-O-tosyl-L-mannofuranose is readily converted by sodium methoxide into methyl 6-deoxy-2,3-0-isopropylidene-/3-D-allofuranoside. In this... 

Participation of the ring-oxygen atom has also been postulated,124 to account for the stereospecific formation of L-mannopyranoside (40) and D-allofuranoside (41) products in the deamination, by way of 39b, of methyl 4-amino-4,6-dideoxy-2,3-0-isopropylidene-a-L-man-nopyranoside (39a). Ring contraction to give furanoside products pre-... 

B. Synthesis of u-Methyl Mannofuranoside and p-Methyl Allofuranoside [38] (Scheme 15)... 

Treatment of methyl 6-deoxy-2,3-0-isopropylidene-5-0-p-tolylsulfonyl-/3-D-allofuranoside (100) with alkoxides in hot alcohol, or with hot soda-lime caused the formation of methyl 5,6-dideoxy-2,3-0-isopropylidene-j8-D-eri/[Pg.111]

Methanesulfonic acid added to an ice-cooled soln. of 5-benzyloxy-l,2-epoxy-4-hydroxy-3-methylhexyl N,N-diisopropylcarbamate in methanol, the mixture stirred at 20-5° for 15 h, and treated with triethylamine methyl 5-0-benzyl-3,6-dideoxy-3-C-methyl-P-L-allofuranoside. Y 84%. F.e.s. D. Hoppe et al.. Synthesis 1989, 83-8 preparation of C- and C-labelled methane-sulfonic and -sulfinic acid s. V.J. Feil et al., J. Labelled Compds. Radiopharm. 25, 1021-5 (1988). 

Me glycoside, 3, 2,4,6-tetra-Ac Methyl 3-acetamido-2,5,6-tri-0-acetyl-3-deoxy-p-D-allofuranoside C15H23NO9 361.348 Syrup, cryst. on standing. Mp 89-90°. [a]o +18.4 (c, 1.2 in CHCI3). 

Allyl glycoside, 2,3-O-isopropylidene Allyl 5-amino-5-deoxy-2,3-0-isopropylidene-P-D-allofuranoside [123168-75-2]... 

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