517893-16-2Relevant articles and documents
A robust synthesis of N-glycolyl muramyl dipeptide via azidonitration/reduction
Xing, Shuo,Gleason, James L.
, p. 1515 - 1520 (2015/01/30)
A novel synthetic route leading to N-glycolyl muramyl dipeptide (MDP), a bacterial glycopeptide of particular interest in studies of nucleotide-binding oligomerization domain-containing protein 2 (NOD2), is described. The synthetic strategy hinges on the alkylation of benzylidene-protected glucal with 2-bromopropionic acid and thus circumvents a challenging and non-reproducible SN2 step at the C-3 position of glucosamine derivatives. The subsequent sequence includes an azidonitration and an unusual azide reduction/acylation step via an aza ylide/oxaphospholidine intermediate. This approach generates a protected N-glycolyl MDP that can be either subjected to a one-step global deprotection or differentially deprotected to obtain further derivatives.
A 3,4-trans-fused cyclic protecting group facilitates α-selective catalytic synthesis of 2-deoxyglycosides
Balmond, Edward I.,Benito-Alifonso, David,Coe, Diane M.,Alder, Roger W.,McGarrigle, Eoghan M.,Galan, M. Carmen
supporting information, p. 8190 - 8194 (2014/08/18)
A practical approach has been developed to convert glucals and rhamnals into disaccharides or glycoconjugates with high α-selectivity and yields (77-97 %) using a trans-fused cyclic 3,4-O-disiloxane protecting group and TsOH·H2O (1 mol %) as a catalyst. Control of the anomeric selectivity arises from conformational locking of the intermediate oxacarbenium cation. Glucals outperform rhamnals because the C6 side-chain conformation augments the selectivity.
Stereoselective synthesis of α-linked 2-deoxy glycosides enabled by visible-light-mediated reductive deiodination
Wang, Hao,Tao, Jinyi,Cai, Xinpei,Chen, Wei,Zhao, Yueqi,Xu, Yang,Yao, Wang,Zeng, Jing,Wan, Qian
supporting information, p. 17319 - 17323 (2015/02/19)
2-Deoxy sugars and their derivatives occur abundantly in many pharmaceutically important natural products. However, the construction of specific 2-deoxy-glycosidic bonds remains as a challenge. Herein, we report an efficient way to prepare 2-deoxy-a-glycosides by glycosylation of 2-iodo-glycosyl acetate and subsequent visible-light-mediated tin-free reductive deiodination. We have successfully applied the postglycosylational-deiodination strategy in the synthesis of more than 30 mono-, di-, tri-, tetra- and pentadeoxysaccharides with excellent stereoselectivity and efficiency. This method has also been applied to the synthesis of a 2-deoxy-tetrasac-charide containing four a-linkages.
A facile synthesis of 4,6-O-benzylidene glucal
Chambers, David J.,Evans, Graham R.,Fairbanks, Antony J.
, p. 1767 - 1769 (2007/10/03)
4,6-O-Benzylidene protected D-glucal, a useful synthetic intermediate, may be accessed from the extremely cheap and readily available starting material α-methyl glucopyranoside, via a simple four-step reaction sequence involving selective triflation and iodide displacement at C-2.
The first radical method for the introduction of an ethynyl group using a silicon tether and its application to the synthesis of 2′-deoxy-2′-C-ethynylnucleosides
Sukeda, Makoto,Ichikawa, Satoshi,Matsuda, Akira,Shuto, Satoshi
, p. 3465 - 3475 (2007/10/03)
A novel radical method for the stereoselective introduction of an ethynyl group has been developed. When a solution of ethynyldimethylsilyl (EDMS) or [2-(trimethylsilyl)ethynyl]dimethylsilyl (TEDMS) ethers of trans-2-iodoindanol was treated with Et3
