7512-03-0Relevant articles and documents
Synthesis of modified D-mannose core derivatives and their impact on GH38 α-mannosidases
Poláková, Monika,Horák, Radim,?esták, Sergej,Holková, Ivana
, p. 62 - 71 (2016/06/01)
Nine new compounds having five- and modified six-member carbohydrate core derived from D-lyxose or D-mannose, and non-hydrolysable aglycones (benzylsulfonyl or aryl(alkyl)triazolyl) were synthesised to investigate their ability to inhibit the recombinant
Nucleophilic displacement-reactions of the 4-sulfonyloxy group in derivatives having the D-manno configuration
Cicero, Daniel,Varela, Oscar,Lederkremer, Rosa M. de
, p. 295 - 308 (2007/10/02)
Methyl 2,3-di-O-benzoyl-6-deoxy-4-O-(p-tolylsulfonyl) and 4-O--α-D-mannopyranosides (9 and 10) were prepared by three different routes from methyl α-D-mannopyranoside (1).The analogous 4-sulfonyloxy derivatives having HO-2 and HO-3 free (14 and 15) were also synthesized from 1.Nucleophilic substitution of the sulfonyloxy group of 9, 10, 14, and 15 by potassium thiocyanate in N,N-dimethylformamide was attempted.Compounds 9 and 10 gave a mixture of solvolysis products: methyl 2,3-di-O-benzoyl-6-deoxy-α-D-talopyranoside (17), methyl 3,4-di-O-benzoyl-6-deoxy-α-D-talopyranoside (18), and methyl 2,4-di-O-benzoyl-6-deoxy-α-D-talopyranoside (19), which are evidently formed by intramolecular displacement of the 4-sulfonate by backside attack of the C-2 benzoyloxy substituent, followed by benzoyl migration.The structure of compounds 17-19 was established by spectroscopic analysis, and then chemically confirmed.Although compound 14 decomposed during the substitution reaction, the 4-p-nitrophenylsulfonyl derivative 15 gave a 2:1 mixture of the 4-thiocyano derivatives with inversion and retention of the C-4 configuration.
New Syntheses of 6-Deoxy-L-gulose and 6-Deoxy-L-talose
Mori, Masami,Tejima, Setsuzo,Niwa, Toshimitsu
, p. 4037 - 4044 (2007/10/02)
Treatment of methyl 2,3,4-tri-O-benzoyl-6-deoxy-6-iodo-α-D-mannopyranoside (1) or methyl 4-O-acetyl-2,3-di-O-benzoyl-6-deoxy-6-iodo-α-D-allopyranoside (11) with silver fluoride in pyridine gave the corresponding D-lyxo- (2) or D-ribo-hex-5-enoside (12), r