4451-35-8Relevant articles and documents
The reactions of β- and α-pyranose peracetates with PCl5, and utilization of the products to construct sarsasapogenin glycosides
Saito,Ichinose,Sasaki,Sumita
, p. 3261 - 3268 (1992)
The reactions of β- and α-pyranose peracetates with PCl5 gave products regioselectively chlorinated. The reactions of 1,2,3,4,6-penta-O-acetyl-β-D-glucopyranose (5) and -β-D-galactopyranose (6) with PCl5 in CCl4 and that of methyl 2,3,4-tri-O-acetyl-β-D-glucuronatopyranose (7) with PCl5 in toluene gave 2-O-trichloroacetyl-β-D-pyranosyl chlorides 4, 12 and 14, respectively, as major products, and α-D-pyranosyl chlorides 11, 13 and 15, respectively, as minor products. On the other hand, the reactions of compounds 8 and 9 which were α-anomers of 5 and 6, respectively, with PCl5 gave as major products transformed acetyl groups at C-6 to -C(Cl) = CCl2 or -C(Cl)2-CCl3 group (16 and 17 from 8 and 18 from 9). The same reaction of 10, which was α-anomer of 7, gave α-chloride 15 as a major product. The glycosidation of sugar derivative 4 with sarsasapogenin 23 gave β-glycoside 24 (29.1%) and α-glycoside 25 (46.9%), and that of 12 with 23 gave β-glycoside 26 (24.0%) and α-glycoside 27 (40.8%). The improvement of the yields of β-glycosides 24 and 26 (66.9 and 62.1% for 24 and 26, respectively) in the glycosidations were accomplished by the employment of α-bromides 28 and 29 obtained from 4 and 6, respectively. The glycosidations of monoglycosides 30 and 31 obtained by the treatment 24 and 26, respectively, with ammonia-saturated ether with sugar acetate bromides 32 and 34 gave diglycoside derivatives 35 and 33, respectively.
2-Trimethylsilylethyl glycosides. Treatment with electrophilic reagents to give trimethylsilyl- and methoxymethyl glucopyranosides and glucopyranosyl chloride
Jansson, Karl,Magnusson, Goeran
, p. 59 - 64 (1990)
Treatment of 2-trimethylsilylethyl 2346-tetra-O-acetyl-β-D-glucopy ranoside (-1) with trimethylsilyl trifluoromethanesulfonate trifluoromethanesulfonic acid or borontrifluoride etherate in the presence ofdimethoxymethane gave methoxymethyl 2346-tetra-O-acetyl-β-D-glucopyranoside in 54 62 and 66% yield respectively. In the absence of dimethoxymethane trimethylsilyl 2346-tetra-O-acetyl-β-D-glucopyranoside was formed in 78% yield. Treatment of I with 11-dichloromethylmethyl ether in the presence of zinc chloride gave 2346-tetra-O-acetyl-α-D-glucopyranosyl chloride in 98% yield.
Stereoselective Preparation of C-Aryl Glycosides via Visible-Light-Induced Nickel-Catalyzed Reductive Cross-Coupling of Glycosyl Chlorides and Aryl Bromides
Mou, Ze-Dong,Wang, Jia-Xi,Zhang, Xia,Niu, Dawen
supporting information, p. 3025 - 3029 (2021/05/27)
A nickel-catalyzed cross-coupling reaction of glycosyl chlorides with aryl bromides has been developed. The reaction proceeds smoothly under visible-light irradiation and features the use of bench-stable glycosyl chlorides, allowing the highly stereoselective synthesis of C-aryl glycosides. (Figure presented.).
Chemoenzymatic synthesis of arabinomannan (AM) glycoconjugates as potential vaccines for tuberculosis
Li, Zhihao,Bavaro, Teodora,Tengattini, Sara,Bernardini, Roberta,Mattei, Maurizio,Annunziata, Francesca,Cole, Richard B.,Zheng, Changping,Sollogoub, Matthieu,Tamborini, Lucia,Terreni, Marco,Zhang, Yongmin
supporting information, (2020/07/27)
Mycobacteria infection resulting in tuberculosis (TB) is one of the top ten leading causes of death worldwide in 2018, and lipoarabinomannan (LAM) has been confirmed to be the most important antigenic polysaccharide on the TB cell surface. In this study, a convenient synthetic method has been developed for synthesizing three branched oligosaccharides derived from LAM, in which a core building block was prepared by enzymatic hydrolysis in flow chemistry with excellent yield. After several steps of glycosylations, the obtained oligosaccharides were conjugated with recombinant human serum albumin (rHSA) and the ex-vivo ELISA tests were performed using serum obtained from several TB-infected patients, in order to evaluate the affinity of the glycoconjugate products for the human LAM-antibodies. The evaluation results are positive, especially compound 21 that exhibited excellent activity which could be considered as a lead compound for the future development of a new glycoconjugated vaccine against TB.
Method for preparing halogenated sugar under mild conditions
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Paragraph 0019-0021; 0055-0060, (2020/07/02)
The invention discloses a method for preparing halogenated sugar under mild conditions. The method comprises the following steps that an easily-prepared thioglycoside donor and a halogen simple substance or halogen intercompound undergo a reaction at room temperature to obtain the halogenated sugar (chlorine, bromine and iodine). The halogen simple substance or the halogen intercompound is commercial easily available iodine elementary substance, iodine bromide and iodine chloride. The method is suitable for various pyranoses and furanoses. The method has no limitation on a protecting group ofthe thioglycoside donor, and the protecting group can be an electron withdrawing group such as acetyl, benzoyl and the like, and can also be an electron donating group such as benzyl, silicon base andthe like. Meanwhile, the reaction can occur in various organic solvents such as dichloromethane, acetonitrile and methylbenzene. The preparation method of the halogenated sugar is simple, reaction conditions are mild, raw materials are easy to obtain, the application range is wide, the halogenated sugar is compatible with acid-labile groups such as isopropylidene ketal and silicon groups, and a pure product can be obtained by removing a solvent from the halogenated sugar which is not stable in the separation process.
