55692-90-5Relevant academic research and scientific papers
Tri-isopropylsilyl thioglycosides as masked glycosyl thiol nucleophiles for the synthesis of S-linked glycosides and glyco-conjugates
Mandal,Nilsson
, p. 4816 - 4819 (2014)
Tri-isopropylsilyl thio-glycosides (TIPS S-glycosides) were synthesized through base promoted SN2 substitution of glycosyl halides with TIPS-SH or by Lewis acid promoted glycosylation of TIPS-SH with glycosyl acetates or p-methoxyphenyl glycosi
Stereoselective synthesis of β-glycosyl thiols and their synthetic applications
Jana, Manas,Misra, Anup Kumar
, p. 2680 - 2686 (2013/04/24)
A significantly fast reaction condition for the exclusive preparation β-glycosyl thiol derivatives has been developed successfully. The reaction condition is one-step, fast, high yielding, highly stereoselective, and requires only benchtop chemicals. Further reaction of glycosyl thiol derivatives with Michael acceptors and alkylating agents furnished thioglycosides and (1,1)-thiolinked trehalose analogs.
Towards dynamic drug design: Identification and optimization of β-galactosidase inhibitors from a dynamic hemithioacetal system
Caraballo, Remi,Sakulsombat, Morakot,Ramstroem, Olof
experimental part, p. 1600 - 1606 (2011/05/06)
A discovery strategy relying on the identification of fragments through resolution of a constitutional dynamic system, coupled to subsequent static ligand design and optimization, is demonstrated. The strategic design and synthesis of the best molecular fragments identified from a dynamic hemithioacetal system into static ligand structures yielded a range of β-galactosidase inhibitors. Two series of structures mimicking the hemithioacetal motif were envisaged: thioglycosides and C-glycosides. Inhibition studies provided important structural information for the two groups, and 1-thiobenzyl-b-d-galactopyranoside demonstrated the best inhibitory effects.
Modified one-pot protocol for the preparation of thioglycosides from unprotected aldoses via S-glycosyl isothiouronium salts
Tiwari, Pallavi,Agnihotri, Geetanjali,Misra, Anup Kumar
, p. 723 - 732 (2007/10/03)
An efficient one-pot protocol for the direct preparation of thioglycosides starting from unprotected reducing sugars via S-glycosyl isothiouronium salts is reported. In this one-pot methodology, BF3·OEt2 has been used as a general catalyst for both per-O-acetylation of sugars and conversion of sugar per-O-acetates into S-glycosyl isothiouronium salts, which was allowed to react with alkylating agents in the presence of a base to furnish thioglycosides in excellent yield. Copyright Taylor & Francis, Inc.
Reaction of sugar thiocyanates with Grignard reagents. New synthesis of thioglycosides
Pakulski, Zbigniew,Pierozynski, Donat,Zamojski, Aleksander
, p. 2975 - 2992 (2007/10/02)
Glycosyl thiocyanates having hydroxyl groups protected with acetyl or benzoyl groups react readily at -40°C with Grignard reagents to afford the corresponding alkyl or aryl thioglycosides in good yields. Monosaccharide derivatives having the SCN grouping at other positions form under similar conditions thioethers. Axial thiocyanates do not react. Elevated temperatures induce side reactions leading to mercaptans.
SYNTHESIS OF 1-THIOGLYCOSIDES IN A CATALYTIC TWO-PHASE SYSTEM
Bogusiak, Jadwiga,Szeja, Wieslaw
, p. 293 - 298 (2007/10/02)
An improved preparation of thioglycosides involves a reaction of 1,2-cis-gluco- and galactopyranosyl bromides with thiols in a catalytic two-phase system.The reaction is considered to proceed according to SN2 mechanism.Formation of orthothioesters is favored for tetra-O-acetyl-β-D-glucopyranosyl chloride and thiophenol.
