2-DEOXY SUGARS .15. 4 ISOMERIC METHYL GLYCOSIDES OF 2-DEOXY-D-RIBO-HEXOSE

被引:10
作者
BHAT, CC
BHAT, KV
ZORBACH, WW
机构
[1] Division of Bio-Organic Chemistry, Gulf South Research Institute, New Iberia, LA 70560
关键词
D O I
10.1016/S0008-6215(00)80462-0
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Brief treatment of 2-deoxy-d-ribo-hexose in methanol with a small proportion of hydrogen chloride resulted in a 100-% yield of crystalline methyl 2-deoxy-α,β-d-ribo-hexofuranoside in an anomeric ratio of 1:1, fractional recrystallization of which resulted in partial separation of the α-d anomer. The furanoside mixture was converted into its tris-p-nitrobenzoate, and, thence, into crystalline 2-deoxy-3,5,6-tri-O-p-nitrobenzoyl-d-ribo-hexosyl bromide. The new halide underwent methanolysis to yield mainly methyl 2-deoxy-β-O-ribo-hexofuranoside. Methanolysis of 2-deoxy-3,4,6-tri-O-p-nitrobenzoyl-α-d-ribo-hexosyl bromide, followed by deacylation, gave the hitherto-unknown methyl 2-deoxy-β-d-ribo-hexopyranoside. Controlled hydrolysis of methyl 4,6-O-benzylidene-2-deoxy-α-d-ribo-hexopyranoside with acid gave crystalline methyl 2-deoxy-α-d-ribo-hexopyranoside, hitherto reported as a syrup. © 1969.
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页码:197 / &
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