68 二,三の天然アシル化糖およびアシル化配糖体の合成 : 糖類に対する位置選択的アシル基の導入
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I. Regio-selective Introduction of an O-Acyl Group to Carbohydrates by Use of Bu_2SnO. Total Syntheses of Inundoside-G and Inundoside-D_1. Selective mono-acylation of some pento- and hexo-pyranosides by using Bu_2SnO was examined in comparison with the results of the (Bu_3Sn)_2O method and direct acylation (Table 1). The Bu_2SnO method was found to be particularly useful in that it selectively activates an equatorial hydroxyl group which bears an oxygenated function (OH or OMe) in a cis relationship at an adjacent position, even in the presence of a more reactive primary OH group. By this method total syntheses of inundoside-G and inundoside-D_1 were achieved. Stannylation of serratenediol-3-α-L-arabinopyranoside (inundoside-A) (1b) with Bu_2SnO followed by p-coumaroylation gave the 3'-O-p-coumarate (inundoside-G)(4b) which on heating in pyridine rearranged to the 4'-O-p-coumarate (inundoside-D_1)(5b). II. A New Synthetic Method for 1-O-Acyl-β-D-glucopyranoses Using Tri-O-trifluoroacetyl-1,6-anhydroglucose. Synthesis of Tuliposide-A. Tri-O-trifluoroacetyl-1,6-anhydroglucose (8) was proved to be an useful precursor of 1β-O-acylglucoses. Treatment of 8 with TiBr_4 in boiling CF_3COOH afforded 2,3,4,6-tetra-O-trifluoroacetyl-α-D-glucopyranosyl bromide, which on reaction with RCOOAg in benzene gave the 1β-O-acyl derivative. The TFA group was removed either by contact with methanol (in presence of Amberlite-IRA-400-HCO_3^-) or by alumina chromatography yielding 1β-O-acyl-D-glucopyranose. By this method tuliposide-A, 1-O-(γ-hydroxy-α-methylenebutyroyl)-β-D-glucopyranose (6b), was synthesized.
- 天然有機化合物討論会の論文
- 1983-09-15
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