93978-95-1Relevant articles and documents
FURANOSE RING ANOMERIZATION: A KINETIC STUDY OF THE 5-DEOXYPENTOSES AND 5-O-METHYLPENTOSES
Snyder, Joseph R.,Serianni, Anthony S.
, p. 13 - 26 (1988)
The anomerzation of 5-deoxy-L-pentoses (1-4) and 5-O-methyl-D-pentoses (5-8) in aqueous solution has been studied by (13)C saturation-transfer n.m.r. (s.t.-n.m.r.) spectroscopy, using compounds substituted with (13)C at the anomeric carbon atom.Unidirectional rate-constants of ring-opening (kopen) and ring closing (kclose) have been obtained for these compounds under identical solution conditions (50mM acetate buffer, pH 4.0 at 60 deg C), and have been compared to those measured for the D-tetroses (9 and 10) and four D-pentose 5-phosphates (11-14).Based on these comparisons, several correlations between furanose structure and reactivity have been revealed, and models have been proposed to explain the observed kinetic behavior of compounds 1-10.The effect of exocyclic structure on acid-catalyzed rate-constants was also examined by comparing the behavior of 5-deoxy-L-lyxose and 5-O-methyl-D-lyxose.Some consideration has been given to identifying the factors (enthalpic and entropic) that may play roles in determining the effect of structure on anomerization reactivity.
Concise total synthesis of two marine natural nucleosides: Trachycladines A and B
Ding, Haixin,Li, Wei,Ruan, Zhizhong,Yang, Ruchun,Mao, Zhijie,Xiao, Qiang,Wu, Jun
, p. 1681 - 1685 (2014/08/18)
We report the first total synthesis of trachycladines A (10 steps, 34.2% overall yield) and B (11 steps, 35.0% overall yield) by using 5-deoxy-1,2,3-tri-O-acetyl-β-D-ribofuranose as the starting material. The critical step was the SnCl4 assisted regio- and steroselective deprotection of perbenzylated 1-O-methyl-5-deoxyribofuranose. The enzyme adenylate deaminase (EC 3.5.4.6) was successfully applied to the chemoenzymatic synthesis of trachycladines B.
The influence of microwave irradiation on stereospecific Mo(VI)-catalyzed transformation of deoxysugars
Hricoviniova, Zuzana
experimental part, p. 1239 - 1242 (2009/11/30)
The stereospecific mutual isomerization of 5-, 6-, and 7-deoxysugars in a microwave field with Mo(VI) as a catalyst is reported. The reaction cycle allows the use of catalytic amounts of molybdate ions to form highly reactive catalytically active dimolybd