84635-36-9Relevant academic research and scientific papers
Dehydrative Thioglycosylation of 1-Hydroxyl Glycosides Catalyzed by In Situ-Generated AlI3
Weng, Shiue-Shien,Hsieh, Kun-Yi,Zeng, Zih-Jian
, p. 464 - 473 (2017/05/19)
Thioglycosylation of 1-hydroxyl glycosides catalyzed by in situ-generated AlI3 from elemental aluminium and molecular iodine has been developed. This method provides an alternative route to access anomeric thioglycosides without the use of hazard Lewis acidic activators or per-modified activated thiol sources. The major advantages of this dehydrative procedure are environmental friendly, ease of operation, high anomeric diastereoselectivity, and mild reaction conditions.
Ortho-Methylphenylthioglycosides as glycosyl building blocks for preactivation-based oligosaccharide synthesis
Peng, Peng,Xiong, De-Cai,Ye, Xin-Shan
supporting information, p. 1 - 8 (2014/01/06)
Thioglycosides are widely used in orthogonal glycosylation, armed-disarmed chemoselective glycosylation, and preactivation-based glycosylation. Nevertheless, aglycon transfer occasionally occurred in the glycosylation process of thioglycosides. This probl
Palladium-catalyzed cross-coupling reaction of thioglycosides with (hetero)aryl halides
Brachet, Etienne,Brion, Jean-Daniel,Messaoudi, Samir,Alami, Mouad
, p. 477 - 490 (2013/05/08)
α- and β-thioglycosides serve as effective nucleophiles for Buchwald-Hartwig cross-coupling reactions using functionalized (hetero)aryl halides. The functional group tolerance on the electrophilic partner is typically high, both benzyl and acetate protect
Diastereoselective thioglycosylation of peracetylated glycosides catalyzed by in situ generated iron(III) iodide from elemental iodine and iron
Weng, Shiue-Shien
supporting information; experimental part, p. 6414 - 6417 (2010/02/28)
A facile in situ preparation of Fe(III) iodide from cheap, abundant elemental iodine and iron metal served as an efficient catalyst for the thioglycosylation of peracetylated glycosides with various alkyl and aryl mercaptans. Due to neighboring participation, the anomerically pure β-thioglycosides were obtained in good to high yields with exclusive diastereocontrol.
Highly diastereoselective thioglycosylation of functionalized peracetylated glycosides catalyzed by MoO2Cl2
Weng, Shiue-Shien,Lin, Yow-Dzer,Chen, Chien-Tien
, p. 5633 - 5636 (2007/10/03)
Among 18 oxometallic species, MoO2Cl2 was found to be the most reactive in catalytic thioglycosylation of O-acetylated glycosides with functionalized thiols in CH2Cl2, leading cleanly to 1,2-trans-thioglycosides with exclusive diastereocontrol. The new catalytic protocol is applicable to a monoglycoside building block and β-(1→6)-S-linked-thiodisaccharide synthesis.
The Fusion Synthesis of Aryl 1-Thioglycosides
Shimadate, Toshisada,Chiba, Sachiyo,Inouye, Kazuko,Iino, Teruhiko,Hosoyama, Yoshiyuki
, p. 3552 - 3554 (2007/10/02)
A simple method for the preparation of aryl 1-thioglycosides is described.The reaction of D-glucose pentaacetate or 2-acetamido-2-deoxy-D-glucose tetraacetate with arenethiols in the presence of zinc chloride under fusion conditions formed their 1-thiogly
