D-呋喃阿洛糖衍生物的合成
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摘要
本文以α-D-葡萄糖(1)为原料,合成了10个D-呋喃阿洛糖衍生物。重点对环状碳酸酯和苄基化等保护基的合成以及选择性除去1,2-氧-异丙叉保护基进行了研究。
通过α-D-葡萄糖(1)的异丙叉保护反应制备了1,2:5,6-氧-二异丙叉基-α-D-呋喃葡萄糖(2),收率50%;以PDC(重铬酸吡啶盐)氧化-硼氢化钠还原反应得到1,2:5,6-氧-二异丙叉基-α-D-呋喃阿洛糖(3),两步收率为58.0%;研究了以稀硫酸(0.5%)做催化剂,选择性水解制备了1,2-氧-异丙叉基-α-D-呋喃阿洛糖(4),收率94.0%。
研究了化合物4和碳酸二乙酯在NaHCO3作用下的酯交换反应,合成了1,2-氧-异丙叉基-α-D-呋喃阿洛糖-5,6碳酸酯(5),收率48.9%;研究了化合物3的乙酰化、选择性水解(2步收率86.3%)得到了3-氧-乙酰基-1,2-氧-异丙叉基-α-D-呋喃阿洛糖化合物(8),化合物8和固体光气反应合成了3-氧-乙酰基-1,2-氧-异丙叉基-α-D-呋喃阿洛糖-5,6碳酸酯(9),收率93.2%;用2,3-二氯-5,6-二氰基-1,4-苯醌(DDQ)做催化剂,在乙腈的水溶液中化合物8和9在不同反应条件下合成了D-呋喃阿洛糖-5,6碳酸酯(6)和3-乙酰基-D-呋喃阿洛糖-5,6-碳酸酯(10),收率分别为67.2%和67.8%。
研究了化合物4的苄基化、氯乙酰化和乙酰化等保护反应,分别合成了3,5,6-氧-三苄基-1,2-氧-异丙叉基-α-D-呋喃阿洛糖(11)、3,5,6-氧-三氯乙酰基-1,2-氧-异丙叉基-α-D-呋喃阿洛糖(13)和3,5,6-氧-三乙酰基-1,2-氧-异丙叉基-α-D-呋喃阿洛糖(15),收率分别是71.6%、94.7%和92.3%;用DDQ做催化剂,用乙腈的水溶液做溶剂,在不同的反应条件下合成了除去了异丙叉保护基的化合物3,5,6-氧-三苄基-D-呋喃阿洛糖(12)、3,5,6-氧-三氯乙酰基-D-呋喃阿洛糖(15)和3,5,6-氧-三乙酰基-D-呋喃阿洛糖(16),收率分别是82.7%、67.6%和65.7%;用10%H2SO4做催化剂,由化合物12也可以合成化合物11 ,收率是87.4%。
本论文中的D-呋喃阿洛糖衍生物5、6和9-16均经1H-NMR鉴定。其中化合物5、6、9、10、13、14和16未见文献报道。
Withα-D-glucose (1) as starting material, ten D-allofuranose derivatives were prepared. Particularly, synthetic methods of cyclic carbonate, benzylation and 1,2-O-isopropylidene group selective hydrolysis were studied intensively.
1,2:5,6-O-diisopropylidene-α-D-gluofuranose (2) was synthesized by isopropylidenation reaction fromα-D-gluofuranose. The yield was 50.1%. 1,2:5,6-O-diisopropylidene-α-D-allofuranose (3) was synthesized by PDC-Ac2O oxidation and NaBH4 reduction. Above two steps overall yield was 58.0%. Selective hydrolysis reaction was studied to synthesize 1,2-O-isopropylidene-α-D-allofuranose (4) with dilute solution of H2SO4 (0.5%). The yield was 94.0%.
In the presence of a catalytic amount of sodium dicarbonate, ester exchange reaction was studied between compound 4 and diethyl carbonate. Thus 1,2-O-isopropylidene-α-D-allofuranose 5,6-carbonate (5) was synthesized with moderate yield (48.9%). 3-O-Acetyl-1,2-O-isopropylidene-α-D-allofuranose 8 was synthesized from 3 by acetylation and selective hydrolysis. Two steps overall yield was 86.3%. Bis(trichlormethyl)carbonate (triphosgene)was used to synthesize 3-O-acetyl-1,2-O- isopropylidene-α-D-allofuranose 5,6-carbonate(9) from compound 8 with high yield (93.2%). In the presence of a catalytic amount of 2,3-dichloro-5,6-dicynao-1,4-benzoquinone(DDQ), D-allofuranose 5,6-carbonate(6) and 3-acetyl-D-allofuranose 5,6-carbonate(10) were synthesized from compound 8 and 9 under different conditions in aqueous acetonitrile.
3,5,6-Tri-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose (11), 3,5,6-tri-O- chloroacetyl-1,2-O-isopropylidene-α-D-allofuranose (13) and 3,5,6-tri-O-acetyl-1,2 -O-isopropylidene-α-D-allofuranose (15) were synthesized from 4 by benzylation, chloroacetylation and acetylation, respectively. The yield was 71.6%, 94.7% and 92.3%, respectively. In the presence of a catalytic amount of 2,3-dichloro-5,6-dicynao -1,4-benzoquinone(DDQ), 3,5,6-tri-O-benzyl-D-allofuranose (12), 3,5,6-tri-O-chloro- acetyl-D-allofuranose (14) and 3,5,6-tri-O-acetyl-D-allofuranose (16) were synthesized from compound 11,13 and 15 under different conditions in aqueous acetonitrile. The yield was 82.7%, 67.6% and 65.7%, respectively. An alternative route was by 10% sulfuric acid hydrolysis from compound 11 to 12 with hige yield 87.4%.
D-Allofuranose derivatives, 5,6 and 9-16,obtained in this paper were characterized by 1H-NMR spectra. Compounds, 5, 6, 9, 10, 13,14 and 16, were not been reported previously.
通过α-D-葡萄糖(1)的异丙叉保护反应制备了1,2:5,6-氧-二异丙叉基-α-D-呋喃葡萄糖(2),收率50%;以PDC(重铬酸吡啶盐)氧化-硼氢化钠还原反应得到1,2:5,6-氧-二异丙叉基-α-D-呋喃阿洛糖(3),两步收率为58.0%;研究了以稀硫酸(0.5%)做催化剂,选择性水解制备了1,2-氧-异丙叉基-α-D-呋喃阿洛糖(4),收率94.0%。
研究了化合物4和碳酸二乙酯在NaHCO3作用下的酯交换反应,合成了1,2-氧-异丙叉基-α-D-呋喃阿洛糖-5,6碳酸酯(5),收率48.9%;研究了化合物3的乙酰化、选择性水解(2步收率86.3%)得到了3-氧-乙酰基-1,2-氧-异丙叉基-α-D-呋喃阿洛糖化合物(8),化合物8和固体光气反应合成了3-氧-乙酰基-1,2-氧-异丙叉基-α-D-呋喃阿洛糖-5,6碳酸酯(9),收率93.2%;用2,3-二氯-5,6-二氰基-1,4-苯醌(DDQ)做催化剂,在乙腈的水溶液中化合物8和9在不同反应条件下合成了D-呋喃阿洛糖-5,6碳酸酯(6)和3-乙酰基-D-呋喃阿洛糖-5,6-碳酸酯(10),收率分别为67.2%和67.8%。
研究了化合物4的苄基化、氯乙酰化和乙酰化等保护反应,分别合成了3,5,6-氧-三苄基-1,2-氧-异丙叉基-α-D-呋喃阿洛糖(11)、3,5,6-氧-三氯乙酰基-1,2-氧-异丙叉基-α-D-呋喃阿洛糖(13)和3,5,6-氧-三乙酰基-1,2-氧-异丙叉基-α-D-呋喃阿洛糖(15),收率分别是71.6%、94.7%和92.3%;用DDQ做催化剂,用乙腈的水溶液做溶剂,在不同的反应条件下合成了除去了异丙叉保护基的化合物3,5,6-氧-三苄基-D-呋喃阿洛糖(12)、3,5,6-氧-三氯乙酰基-D-呋喃阿洛糖(15)和3,5,6-氧-三乙酰基-D-呋喃阿洛糖(16),收率分别是82.7%、67.6%和65.7%;用10%H2SO4做催化剂,由化合物12也可以合成化合物11 ,收率是87.4%。
本论文中的D-呋喃阿洛糖衍生物5、6和9-16均经1H-NMR鉴定。其中化合物5、6、9、10、13、14和16未见文献报道。
Withα-D-glucose (1) as starting material, ten D-allofuranose derivatives were prepared. Particularly, synthetic methods of cyclic carbonate, benzylation and 1,2-O-isopropylidene group selective hydrolysis were studied intensively.
1,2:5,6-O-diisopropylidene-α-D-gluofuranose (2) was synthesized by isopropylidenation reaction fromα-D-gluofuranose. The yield was 50.1%. 1,2:5,6-O-diisopropylidene-α-D-allofuranose (3) was synthesized by PDC-Ac2O oxidation and NaBH4 reduction. Above two steps overall yield was 58.0%. Selective hydrolysis reaction was studied to synthesize 1,2-O-isopropylidene-α-D-allofuranose (4) with dilute solution of H2SO4 (0.5%). The yield was 94.0%.
In the presence of a catalytic amount of sodium dicarbonate, ester exchange reaction was studied between compound 4 and diethyl carbonate. Thus 1,2-O-isopropylidene-α-D-allofuranose 5,6-carbonate (5) was synthesized with moderate yield (48.9%). 3-O-Acetyl-1,2-O-isopropylidene-α-D-allofuranose 8 was synthesized from 3 by acetylation and selective hydrolysis. Two steps overall yield was 86.3%. Bis(trichlormethyl)carbonate (triphosgene)was used to synthesize 3-O-acetyl-1,2-O- isopropylidene-α-D-allofuranose 5,6-carbonate(9) from compound 8 with high yield (93.2%). In the presence of a catalytic amount of 2,3-dichloro-5,6-dicynao-1,4-benzoquinone(DDQ), D-allofuranose 5,6-carbonate(6) and 3-acetyl-D-allofuranose 5,6-carbonate(10) were synthesized from compound 8 and 9 under different conditions in aqueous acetonitrile.
3,5,6-Tri-O-benzyl-1,2-O-isopropylidene-α-D-allofuranose (11), 3,5,6-tri-O- chloroacetyl-1,2-O-isopropylidene-α-D-allofuranose (13) and 3,5,6-tri-O-acetyl-1,2 -O-isopropylidene-α-D-allofuranose (15) were synthesized from 4 by benzylation, chloroacetylation and acetylation, respectively. The yield was 71.6%, 94.7% and 92.3%, respectively. In the presence of a catalytic amount of 2,3-dichloro-5,6-dicynao -1,4-benzoquinone(DDQ), 3,5,6-tri-O-benzyl-D-allofuranose (12), 3,5,6-tri-O-chloro- acetyl-D-allofuranose (14) and 3,5,6-tri-O-acetyl-D-allofuranose (16) were synthesized from compound 11,13 and 15 under different conditions in aqueous acetonitrile. The yield was 82.7%, 67.6% and 65.7%, respectively. An alternative route was by 10% sulfuric acid hydrolysis from compound 11 to 12 with hige yield 87.4%.
D-Allofuranose derivatives, 5,6 and 9-16,obtained in this paper were characterized by 1H-NMR spectra. Compounds, 5, 6, 9, 10, 13,14 and 16, were not been reported previously.
引文
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