Journal of the Chemical Society. Perkin transactions II p. 525 - 530 (1986)
Update date:2022-09-26
Topics:
Seela, Frank
Menkhoff, Sabine
Behrendt, Silvia
2'-Deoxy-2-methoxytubercidin (6a) which was prepared from the nucleobase (1a) with the halogenose (2) via phase-transfer glycosylation isomerizes rapidly under acidic conditions.Two pyranosides <(7a) and (8a)> and the anomeric furanoside (5a) are formed.The isomerization process was followed kinetically, demonstrating that furanoside formation is kinetically controlled whereas the β-pyranoside (7a) is the thermodynamically most stable product.From 2'-deoxytubercidin (6b) similar results were obtained but isomerization was slow, compared with (6a).The ribonucleoside tubercidin (6c) did isomerize only under vigorous acid treatment leading to the α-furanoside (5c) and the nucleobase (1c) by cleavage of the N-glycosylic bond.
View MoreLandz International Company Ltd.
Contact:0086-21-58891610
Address:985 Dongfang Road, Pudong, Shanghai 200122 China
Shanghai birch chemical technology co.,ltd
Contact:+86-21-54096810
Address:No.2588,Jungong Road,Shanghai,China
Contact:+86-27-87204219, +86-27-87215023
Address:2402, HuiGu Space-time Building, 8 Forest Road, East Lake Hi-Tech Development Zone
Contact:--
Address:80G, No.1 Building, Guodu Development Mansion, No. 182 Zhaohui Road, Hangzhou City, Zhejiang Province,China.
Doi:10.1139/v79-120
(1979)Doi:10.1016/j.tetlet.2008.03.096
(2008)Doi:10.1021/ja802982h
(2008)Doi:10.1016/0022-328X(85)80305-3
(1985)Doi:10.1039/c1gc15707h
(2011)Doi:10.1055/s-0030-1259905
(2011)
